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100-49-2

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100-49-2 Usage

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 100-49-2 differently. You can refer to the following data:
1. Cyclohexanemethanol used as solvents, fuels . It is also used in pharmaceuticals, plasticizers, surfactants, lubricants, ore floatation agents, hydraulic fluids, and detergents.
2. Cyclohexanemethanol (Cyclohexyl methanol) can be used as a starting material for the synthesis of cyclohexanecarboxaldehyde, cyclohexanecarboxylic acid, cyclohexanone, and 1,4-cyclohexadione by photocatalytic oxidation (PCO) using titanium dioxide nanoparticles as a catalyst.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 1059, 1995 DOI: 10.1016/0040-4039(94)02453-I

Check Digit Verification of cas no

The CAS Registry Mumber 100-49-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 100-49:
(5*1)+(4*0)+(3*0)+(2*4)+(1*9)=22
22 % 10 = 2
So 100-49-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H14O/c8-6-7-4-2-1-3-5-7/h7-8H,1-6H2

100-49-2 Well-known Company Product Price

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  • USP

  • (1154605)  Cyclohexylmethanol  United States Pharmacopeia (USP) Reference Standard

  • 100-49-2

  • 1154605-2X1ML

  • 4,326.66CNY

  • Detail

100-49-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclohexanemethanol

1.2 Other means of identification

Product number -
Other names Cyclohexylmethanol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100-49-2 SDS

100-49-2Synthetic route

benzyl alcohol
100-51-6

benzyl alcohol

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With hydrogen In water at 100℃; under 15001.5 Torr; for 1h;100%
With hydrogen In water at 100℃; under 22502.3 Torr; for 3h;99%
With hydrogen; tetra(n-butyl)ammonium hydrogensulfate; rhodium colloidal catalyst In water at 36℃; under 180018 Torr; for 62h; pH=7.5; Catalytic hydrogenation;73%
cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 25℃; for 2h;100%
With isopropyl alcohol; zirconium(IV) oxide for 6h; Heating;99%
With isopropyl alcohol; zirconium(IV) oxide for 6h; Rate constant; Heating;99%
benzaldehyde
100-52-7

benzaldehyde

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With hydrogen In water at 100℃; under 15001.5 Torr; for 1h;100%
With hydrogen In water at 75℃; under 22502.3 Torr; for 10h; Autoclave; Sealed tube; Ionic liquid; chemoselective reaction;100%
With hydrogen at 180℃; under 150015 Torr; for 10h; Conversion of starting material;
With hydrogen In water at 30℃; under 22502.3 Torr; for 1h; Autoclave; chemoselective reaction;
With hydrogen In water at 30℃; for 19h; Autoclave;
Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With samarium diiodide; hexanal; samarium(III) trifluoromethanesulfonate In tetrahydrofuran; methanol; potassium hydroxide at 20℃; for 0.075h; Reduction;99%
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;94%
With hydrogen; Rh/Al2O3; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 150℃; under 76000 Torr; for 16h;93%
(tetrahydropyranoxymethyl)-cyclohexane
88773-82-4

(tetrahydropyranoxymethyl)-cyclohexane

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
Nafion-H In methanol for 4h;99%
benzoic acid
65-85-0

benzoic acid

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With hydrogen; Rh/Al2O3; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 150℃; under 76000 Torr; for 16h;99%
With hydrogen In hexane at 130℃; under 15001.5 Torr; for 18h; Molecular sieve; chemoselective reaction;72 %Chromat.
With hydrogen In water at 220℃; under 37503.8 Torr; for 24h; Autoclave;94.6 %Chromat.
cyclohexylmethyl acetate
937-55-3

cyclohexylmethyl acetate

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With methanol; potassium permanganate; trimethylsulphonium iodide at 25℃; under 760.051 Torr; chemoselective reaction;99%
With ((N-((6-((di-tert-butylphosphino)methyl)pyridin-2-yl)methyl)-2-methylpropan-2-amine))CoCl2; potassium tert-butylate; hydrogen; sodium triethylborohydride In tetrahydrofuran at 130℃; under 37503.8 Torr; for 48h; Inert atmosphere; Autoclave; High pressure;51 %Chromat.
With C21H35BrMnN2O2P; hydrogen; potassium hydride; 1,3,5-trimethyl-benzene In toluene at 100℃; under 15001.5 Torr; for 43h; Autoclave; Inert atmosphere;99 %Spectr.
ethyl cyclohexanecarboxylate
3289-28-9

ethyl cyclohexanecarboxylate

A

ethanol
64-17-5

ethanol

B

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Inert atmosphere; Glovebox;A n/a
B 99%
With C30H37ClN4ORu; hydrogen; sodium t-butanolate In toluene at 105℃; under 4500.45 Torr; for 20h; Glovebox; Sealed tube; Overall yield = 99 %;
methyl cyclohexylcarboxylate
4630-82-4

methyl cyclohexylcarboxylate

A

methanol
67-56-1

methanol

B

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Inert atmosphere; Glovebox;A n/a
B 99%
With C30H37ClN4ORu; hydrogen; sodium t-butanolate In toluene at 105℃; under 4500.45 Torr; for 20h; Glovebox; Sealed tube; Overall yield = >99 %;
methyl cyclohex-1-ene-1-carboxylate
18448-47-0

methyl cyclohex-1-ene-1-carboxylate

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With C13H34BFeNOP2; hydrogen In tetrahydrofuran at 100℃; under 22502.3 Torr; for 18h; Autoclave; Inert atmosphere;98%
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); hydrogen In tetrahydrofuran at 120℃; under 22502.3 Torr; for 19h; Autoclave;85 %Chromat.
3-hydroxymethylcyclohexene
103668-33-3, 3309-97-5

3-hydroxymethylcyclohexene

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With hydrogen; nickel In ethanol at 20℃; under 18240 Torr; for 1.5h;97%
With formic acid In water at 140℃; under 3750.38 Torr; for 4h; Inert atmosphere;
aniline
62-53-3

aniline

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

A

N-(cyclohexylmethyl)aniline
79952-92-4

N-(cyclohexylmethyl)aniline

B

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
Stage #1: aniline; cyclohexanecarbaldehyde at 25℃; for 0.166667h;
Stage #2: With sodium tetrahydroborate; benzoic acid at 25℃; for 0.333333h;
A 97%
B n/a
Stage #1: cyclohexanecarbaldehyde at 40℃; for 0.166667h;
Stage #2: aniline With sodium tetrahydroborate at 40℃; for 3h;
Stage #3: With methanol at 0℃; for 0.5h; chemoselective reaction;
S-phenyl cyclohexanecarbothioate
58587-03-4

S-phenyl cyclohexanecarbothioate

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 19h; Ambient temperature;96%
cyclohexanylcarbonyl chloride
2719-27-9

cyclohexanylcarbonyl chloride

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With butyltriphenylphosphonium tetrahydroborate at 20℃; for 0.0333333h;96%
With zinc(II) tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; diethyl ether at 0℃; for 5h;93%
With zinc(II) tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In diethyl ether at 0℃; for 6h;93%
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 20 °C / Inert atmosphere
2: sodium 2-methyl-2-adamantoxide; sodium hydride; dichlorobis(dicyclohexylphosphinomethylpyridine)-ruthenium (II); hydrogen / toluene; mineral oil / 48 h / 160 °C / 60006 Torr / Inert atmosphere; Autoclave
View Scheme
methyl cyclohexylcarboxylate
4630-82-4

methyl cyclohexylcarboxylate

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With dimethylsulfide borane complex In 2-methyltetrahydrofuran at 90℃; under 7500.75 Torr; for 0.333333h; Inert atmosphere; Flow reactor;95%
Stage #1: methyl cyclohexylcarboxylate With 3-phenyl-propionaldehyde; diethylaluminum benzenethiolate In hexane; toluene at -78℃; for 1.08333h; Inert atmosphere;
Stage #2: With diisobutylaluminium hydride In hexane; toluene at -78 - 0℃; Inert atmosphere;
Stage #3: With hydrogenchloride In hexane; water; toluene at 0℃; chemoselective reaction;
93%
With C18H28Br2N4Ru; potassium tert-butylate; hydrogen In 1,4-dioxane at 105℃; under 22502.3 Torr; for 8h;93%
cyclohexylmethyl trifluoroacetate
164071-20-9

cyclohexylmethyl trifluoroacetate

A

2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

B

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 48h; Glovebox; Inert atmosphere;A 95%
B n/a
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen In toluene at 110℃; under 52505.3 Torr; for 17h; Catalytic behavior; Solvent; Temperature; Inert atmosphere; Glovebox;
4-methoxy-aniline
104-94-9

4-methoxy-aniline

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

A

N-cyclohexylmethyl-p-anisidine
6709-45-1

N-cyclohexylmethyl-p-anisidine

B

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
Stage #1: 4-methoxy-aniline; cyclohexanecarbaldehyde at 25℃; for 0.166667h;
Stage #2: With sodium tetrahydroborate; boric acid at 25℃; for 0.333333h;
A 94%
B n/a
C15H29BO

C15H29BO

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With sodium hydroxide In water Inert atmosphere;94%
ethyl cyclohexanecarboxylate
3289-28-9

ethyl cyclohexanecarboxylate

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With ethylmagnesium bromide; poly(methylhydrosiloxane); bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran; diethyl ether for 5h; Ambient temperature;93%
With lithium borohydride In diethyl ether; toluene at 100℃; for 1h;91%
With potassium borohydride; hafnium tetrachloride In tetrahydrofuran at 40℃; for 10.5h; Inert atmosphere; Cooling with ice;86%
cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
Stage #1: cyclohex-3-enylmethanol With pyridinium p-toluenesulfonate In 1,2-dichloro-ethane at 80℃; for 20h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 6h;
Stage #3: With trifluoroacetic acid In methanol; dichloromethane at 140℃; for 0.0666667h; microwave irradiation; Further stages.;
93%
Multi-step reaction with 2 steps
1: 66 percent / 4-dimethylaminopyridine; Et3N / CH2Cl2 / 24 h / 20 °C
2: 74 percent / H2 / Pd/C / methanol / 24 h / 20 °C
View Scheme
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); water; hydrogen In 1,4-dioxane at 140℃; under 7500.75 Torr; for 18h; Autoclave;93%
With formaldehyd; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water; toluene at 90℃;87%
carbon monoxide
201230-82-2

carbon monoxide

cyclohexene
110-83-8

cyclohexene

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With mer-[(1,4-bis(diphenylphosphino)butane)aquatrichlororuthenium(III)]; hydrogen In tetrahydrofuran at 160℃; under 67506.8 Torr; for 24h; Catalytic behavior;92%
With dodecacarbonyl-triangulo-triruthenium; 2-(dicyclohexylphosphino)-1-methyl-1H-imidazole; water; hydrogen; lithium chloride In 1-methyl-pyrrolidin-2-one at 130℃; under 60 Torr; for 20h; Autoclave; regioselective reaction;76%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 2-(dicyclohexylphosphanyl)-1-(2-methoxyphenyl)-1H-imidazole; hydrogen In toluene at 160℃; under 37503.8 Torr; for 24h; Autoclave; Inert atmosphere; regioselective reaction;51%
With hydrogen; cobalt(II) acetylacetonate dihydrate at 99.9℃; under 84756.7 Torr; for 7h;
cyclohexylcarboxamide
1122-56-1

cyclohexylcarboxamide

A

cyclohexylmethylamine
3218-02-8

cyclohexylmethylamine

B

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With hydrogen at 160℃; under 75007.5 Torr;A 91%
B 8%
With dodecacarbonyl-triangulo-triruthenium; hydrogen; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 160℃; under 75007.5 Torr; for 16h; Inert atmosphere;
With hydrogen In 1,2-dimethoxyethane at 160℃; under 75007.5 Torr; for 16h;
With 5 wt% ruthenium/carbon; water; hydrogen at 59.84℃; under 60006 Torr; for 4h; Reagent/catalyst; Autoclave; Sealed tube;
cyclohexylcarboxamide
1122-56-1

cyclohexylcarboxamide

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;91%
With hydrogen In toluene at 160℃; under 45004.5 Torr; for 15h; Catalytic behavior; Autoclave;76%
With water; hydrogen at 59.84℃; under 60006 Torr; for 48h; Reagent/catalyst; Temperature; Concentration; Pressure; Autoclave; Sealed tube;
Multi-step reaction with 2 steps
1: hydrogen; water / 4 h / 59.84 °C / 60006 Torr / Autoclave; Sealed tube
2: hydrogen / water / 24 h / 59.84 °C / 60006 Torr
View Scheme
S-benzyl cyclohexanecarbothioate
54829-38-8

S-benzyl cyclohexanecarbothioate

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 24h; Ambient temperature;90%
cyclohexylmethyl trimethylsilyl ether
88773-80-2

cyclohexylmethyl trimethylsilyl ether

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With Nafion-H(R); silica gel In hexane at 20℃; for 0.333333h;90%
methyl cyclohex-3-ene-1-carboxylate
6493-77-2

methyl cyclohex-3-ene-1-carboxylate

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With C30H26Cl2N3PRu; hydrogen; sodium ethanolate In toluene at 80℃; under 38002.6 Torr; for 16h; Catalytic behavior; Autoclave; Inert atmosphere; Schlenk technique;90%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

A

methyl cyclohexylcarboxylate
4630-82-4

methyl cyclohexylcarboxylate

B

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

C

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With hydrogen; Aliquat 336; rhodium(III) chloride In water; 1,2-dichloro-ethane at 30℃; under 760 Torr; for 5h;A 89%
B 10 % Chromat.
C 1%
With hydrogen; Aliquat 336; rhodium(III) chloride In water; 1,2-dichloro-ethane at 30℃; under 760 Torr; for 5h;A 89 % Chromat.
B 10%
C 1%
carbon monoxide
201230-82-2

carbon monoxide

1-iodocyclohexane
626-62-0

1-iodocyclohexane

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
Stage #1: carbon monoxide; Cyclohexyl iodide With diethoxymethylane; [CuCl(IPrMe)]; lithium methanolate In tetrahydrofuran at 60℃; under 2280.15 Torr; for 16h; Sealed tube;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; diethyl ether at 20℃; for 2h;
89%
With 2,2'-azobis(isobutyronitrile); triphenylgermane; sodium cyanoborohydride In tetrahydrofuran; benzene at 105℃; under 72400.7 Torr;62%
With tetrabutylammonium borohydride In acetonitrile at 25℃; under 760.051 Torr; for 3h; UV-irradiation;36%
With tetrabutylammonium tricarbonylnitrosyl ferrate; sodium trimethoxyborohydride In tetrahydrofuran at 50℃; under 3040 Torr; Product distribution;
cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; 1-(diacetoxyiodo)-4-methylbenzene In chloroform at 20℃; for 24h;100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; copper(I) bromide dimethylsulfide complex In chlorobenzene at 80℃; for 8h;99%
With sodium hydrogencarbonate; sodium bromide In dichloromethane at 20℃; Electrochemical reaction;99%
cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
ConditionsYield
With peracetic acid; C24H29INO5 In acetic acid at 30℃; for 24h;100%
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In water; acetonitrile at 20℃;96%
With sodium bromate; 4 In water at 60℃; for 15h;95%
2,3,4,6-tetra-O-benzyl-D-glucopyranose
6564-72-3

2,3,4,6-tetra-O-benzyl-D-glucopyranose

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-cyclohexylmethoxy-tetrahydro-pyran

(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-cyclohexylmethoxy-tetrahydro-pyran

Conditions
ConditionsYield
With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane at 22 - 28℃; for 16h; Product distribution; other alcohols; var. time and reaction conditions;100%
With trimethylsilyl bromide; 4 A molecular sieve; tetrabutylammomium bromide; cobalt(II) bromide In dichloromethane at 22 - 28℃; for 16h;100%
cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

cyclohexylmethyl cyclohexanecarboxylate
2611-02-1

cyclohexylmethyl cyclohexanecarboxylate

Conditions
ConditionsYield
With oxygen at 60℃; under 760.051 Torr; for 24h; Irradiation;100%
With iodine; potassium carbonate In tert-butyl alcohol at 20℃; for 27h;93%
With pyridinium hydrobromide perbromide In water at 20℃; for 14h;92%
N-t-butoxycarbonyl-N-methyl-β-alanine
124072-61-3

N-t-butoxycarbonyl-N-methyl-β-alanine

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

benzyl alcohol
100-51-6

benzyl alcohol

Boc-MeβAla-OCH2cHex
654651-68-0

Boc-MeβAla-OCH2cHex

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;100%
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

N-succinimidyl carbonic acid cyclohexylmethyl ester
922723-33-9

N-succinimidyl carbonic acid cyclohexylmethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
C19H28N2O4Si

C19H28N2O4Si

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

C26H40N2O4Si

C26H40N2O4Si

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide at 20 - 50℃; Inert atmosphere;100%
(S)-4-(3-(tert-butyldimethylsilyloxy)phenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxylic acid
1224680-14-1

(S)-4-(3-(tert-butyldimethylsilyloxy)phenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxylic acid

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

C26H40N2O4Si
1224680-16-3

C26H40N2O4Si

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 50℃; Inert atmosphere;100%
C19H28N2O4Si
1365387-40-1

C19H28N2O4Si

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

C26H40N2O4Si
1365387-46-7

C26H40N2O4Si

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 50℃; Inert atmosphere;100%
2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride
146176-60-5

2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

cyclohexylmethyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate

cyclohexylmethyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: cyclohexylmethyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere;
100%
3-bromo-4-fluoropyridine
116922-60-2

3-bromo-4-fluoropyridine

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

3-bromo-4-(cyclohexylmethoxy)pyridine

3-bromo-4-(cyclohexylmethoxy)pyridine

Conditions
ConditionsYield
Stage #1: cyclohexylmethyl alcohol With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.75h;
Stage #2: 3-bromo-4-fluoropyridine In dimethyl sulfoxide for 3h;
100%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

cyclohexylmethyl methanesulfonate
14100-97-1

cyclohexylmethyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;99%
With triethylamine In dichloromethane at 0℃; for 16h;96%
With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;96%
(1S,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-phenylsulfanyl-2-oxa-5-thia-bicyclo[2.2.2]octane
130427-27-9

(1S,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-phenylsulfanyl-2-oxa-5-thia-bicyclo[2.2.2]octane

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

(1S,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-cyclohexylmethoxy-2-oxa-5-thia-bicyclo[2.2.2]octane
130427-34-8

(1S,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-cyclohexylmethoxy-2-oxa-5-thia-bicyclo[2.2.2]octane

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane at -40℃; for 0.166667h; MS 4A;99%
Phenyl 2-deoxy-3,4-O-isopropylidene-1-thio-D-fucopyranoside
139190-72-0, 139190-74-2, 139190-75-3

Phenyl 2-deoxy-3,4-O-isopropylidene-1-thio-D-fucopyranoside

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

(3aS,4R,6S,7aR)-6-Cyclohexylmethoxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran
139190-77-5

(3aS,4R,6S,7aR)-6-Cyclohexylmethoxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane a.) 0 deg C, 1 h, b.) 25 deg C, 16 h;99%
With N-Bromosuccinimide In dichloromethane a.) 0 deg C, 1 h, b.) 25 deg C, 16 h; effect of conformational assistance of the glycosyl donor on stereoselective glycosylation, other glycosyl donors, other alcohols, other solvents;99%
vinyl acetate
108-05-4

vinyl acetate

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

cyclohexylmethyl acetate
937-55-3

cyclohexylmethyl acetate

Conditions
ConditionsYield
With Cp*2Sm(THF)2 In toluene for 0.000833333h; Ambient temperature;99%
cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose
357940-81-9

1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose

(2R,3R,4S,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-cyclohexylmethoxy-tetrahydro-pyran

(2R,3R,4S,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-cyclohexylmethoxy-tetrahydro-pyran

Conditions
ConditionsYield
With 5 Angstroem MS; Sulfate; zirconium(IV) oxide In diethyl ether at 25℃; for 3h;99%
glycine-glycine-glycine
556-33-2

glycine-glycine-glycine

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

[2-(2-amino-acetylamino)-acetylamino]-acetic acid cyclohexylmethyl ester; compound with toluene-4-sulfonic acid

[2-(2-amino-acetylamino)-acetylamino]-acetic acid cyclohexylmethyl ester; compound with toluene-4-sulfonic acid

Conditions
ConditionsYield
In toluene for 3h; Heating;99%
1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

2,4-dichloro-6-cyclohexylmethoxy-[1,3,5]triazine
502767-34-2

2,4-dichloro-6-cyclohexylmethoxy-[1,3,5]triazine

Conditions
ConditionsYield
With potassium hydrogencarbonate In toluene99%
With potassium hydrogencarbonate; 18-crown-6 ether In toluene99%
With potassium carbonate; 18-crown-6 ether In toluene for 18h; Heating / reflux;99%
With potassium hydrogencarbonate; 18-crown-6 ether In toluene for 18h; Heating / reflux;
With potassium hydrogencarbonate; 18-crown-6 ether In toluene for 18h; Heating / reflux;
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

N-(cyclohexylmethyl)-4-methylbenzenesulfonamide
86328-85-0

N-(cyclohexylmethyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With potassium hydroxide In toluene at 130℃; for 96h; Inert atmosphere;99%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium tert-butylate In toluene for 17h; Inert atmosphere; Reflux;97%
With [(η5-C5Me5)Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)]OTf2; caesium carbonate In water at 120℃; for 15h; Inert atmosphere; Schlenk technique;85%
3,5,6-Trichloro-2-hydroxybenzoic acid
40932-60-3

3,5,6-Trichloro-2-hydroxybenzoic acid

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

C14H15Cl3O3

C14H15Cl3O3

Conditions
ConditionsYield
titanium (IV) oxide bis(2,4-pentanedionate) In xylene Reflux;99%
diethylphosphonoacetic acid
3095-95-2

diethylphosphonoacetic acid

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

cyclohexylmethyl 2-(diethoxyphosphoryl)acetate

cyclohexylmethyl 2-(diethoxyphosphoryl)acetate

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere;99%
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

bis(cyclohexylmethyl)-(2E)-but-2-endioate

bis(cyclohexylmethyl)-(2E)-but-2-endioate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 24h; Reflux;99%

100-49-2Relevant articles and documents

Iron catalysed selective reduction of esters to alcohols

Tamang, Sem Raj,Cozzolino, Anthony F.,Findlater, Michael

, p. 1834 - 1838 (2019)

The reaction of (dppBIAN)FeCl2 with 3 equivalents of n-BuLi affords a catalytically active anionic Fe complex; the nature of the anionic complex was probed using EPR and IR experiments and is proposed to involve a dearomatized, radical, ligand scaffold. This complex is an active catalyst for the hydrosilylation of esters to afford alcohols; loadings as low as 1 mol% were employed.

A visible-light-driven transfer hydrogenation on CdS nanoparticles combined with iridium complexes

Li, Jun,Yang, Jinhui,Wen, Fuyu,Li, Can

, p. 7080 - 7082 (2011)

A visible-light-driven transfer hydrogenation of carbonyl and CC compounds has been developed by coupling CdS nanoparticles with iridium complexes, exhibiting high activities, excellent selectivities and a unique pH-dependent catalytic activity.

Highly selective and efficient hydrogenation of carboxylic acids to alcohols using titania supported Pt catalysts

Manyar, Haresh G.,Paun, Cristina,Pilus, Rashidah,Rooney, David W.,Thompson, Jillian M.,Hardacre, Christopher

, p. 6279 - 6281 (2010)

Selective hydrogenation of carboxylic acids to alcohols and alkanes has been achieved under remarkably mild reaction temperatures and H2 pressures (333 K, 0.5 MPa) using Pt/TiO2 catalyst.

Catalytic hydrogenation products of aromatic and aliphatic dicarboxylic acids

Shinde, Sunil B.,Deshpande, Raj M.

, p. 1137 - 1142 (2019)

Hydrogenation of aromatic dicarboxylic acids gave 100 % selectivity to respective cyclohexane dicarboxylic acid with 5 % Pd/C catalyst. 5 % Ru/C catalyst was observed to give over hydrogenation products at 493 K and at lower temperature (453 K) the selectivity for cyclohexane dicarboxylic acids was increased. Hydrogenation of phthalic acid with Ru-Sn/Al2O3 catalyst was observed to give phthalide instead of 1,2-benzene dimethanol or 2-hydroxy methyl benzoic acid. Ru-Sn/Al2O3 catalyst selectively hydrogenated the carboxylic group of cyclohexane dicarboxylic acids to give cyclohexane dimethanol. Use of proper catalysts and reaction conditions resulted in desired products.

On water and in air: Fast and highly chemoselective transfer hydrogenation of aldehydes with iridium catalysts

Wu, Xiaofeng,Liu, Jianke,Li, Xiaohong,Zanotti-Gerosa, Antonio,Hancock, Fred,Vinci, Daniele,Ruan, Jiwu,Xiao, Jianliang

, p. 6718 - 6722 (2006)

(Chemical Equation Presented) Water as solvent: A fast, selective, and high-yielding transfer hydrogenation of a wide range of aldehydes is achieved using IrIII catalysts containing simple ethylene-diamine (en) ligands (see scheme; Ts = p-toluenesulfonyl, TOF = turnover frequency). This procedure is suitable for aldehydes with a wide range of functional groups.

Iron-catalyzed reduction of carboxylic esters to alcohols

Junge, Kathrin,Wendt, Bianca,Zhou, Shaolin,Beller, Matthias

, p. 2061 - 2065 (2013)

A novel catalytic system formed from Fe(stearate)2/NH 2CH2CH2NH2 and polymethylhydrosiloxane was directly developed for the hydrosilylation of carboxylic acid esters to alcohols. The catalytic method exhibits broad substrate scope, including 20 aliphatic, aromatic, and heterocyclic esters. The corresponding alcohols are obtained in moderate to very good yields. The first iron-catalyzed hydrosilylation of carboxylic acid esters to alcohols is described. A catalytic system formed by Fe(stearate)2/NH 2CH2CH2NH2 and polymethylhydrosiloxane (PMHS) is used for this transformation, which has a broad substrate scope, including 20 aliphatic, aromatic, and heterocyclic esters. The corresponding alcohols are obtained in moderate to very good yields. Copyright

Selective Reductions. 30. Effect of Cation and Solvent on the Reactivity of Saline Borohydrides for Reduction of Carboxylic Esters. Improved Procedures for the Conversion of Esters to Alcohols by Metal Borohydrides

Brown, Herbert C.,Narasimhan, S.,Choi, Yong Moon

, p. 4702 - 4708 (1982)

A comparative study of the relative reactivity of saline borohydrides (Li, Na, Ca) for the reduction of carboxylic esters has been made in selected solvents (ether, tetrahydrofuran, diglyme, 2-propanol, and ethanol) at 25 deg C.In ether solvents the reactivity follows the trend LiBH4 > Ca(BH4)2 > NaBH4.On the other hand, in alcohol solvents the order of reactivity is Ca(BH4)2 > LiBH4 > NaBH4.The reactivities of LiBH4 in ethyl ether and THF, of Ca(BH4)2 in THF and 2-propanol, and of NaBH4 in ethanol proved to be promising for the reduction of esters.However, alcoholsolvents are not useful for reductions at elevated temperatures because the decomposition of the reagents becomes competitive with the reduction.A convenient synthetic procedure has been developed for the rapid conversion of esters to alcohols by using LiBH4 in ethyl ether, LiBH4 in THF, and Ca(BH4)2 in THF and utilizing essentially stoichiometric amounts of the reagents.The procedure involves adding toluene to the reaction mixture and bringing the temperature to 100 deg C while allowing the solvent do distill off.Following completion of the reaction, toluene is readily removed under vacuum and the reaction product hydrolyzed.These reductions were generally complete in 0.5 - 2.0 h, and high yields of alcohols (73-96percent) were isolated.A number of ester derivatives, including compounds containing nitro, halo, cyano, and alkoxy groups, diesters, and lactones were reduced by this procedure.The study demonstrated the high selectivity of these reagents, permitting the rapid reduction of the ester group in the presence of many substituents.However, unsaturated esters undergo simultaneous hydroboration when reduced by this procedure.

Stable and easily handled FeIII catalysts for hydrosilylation of ketones and aldehydes

Zhu, Kailong,Shaver, Michael P.,Thomas, Stephen P.

, p. 2119 - 2123 (2015)

The amine-bis(phenolate) iron(III)-catalysed reduction of ketones and aldehydes to the corresponding secondary and primary alcohols by a consecutive hydrosilylation/hydrolysis process is reported. The amine-bis(phenolate) iron(III) catalyst is easily accessible, stable towards moisture and air and has a broad substrate scope.

Discrete iron complexes for the selective catalytic reduction of aromatic, aliphatic, and α,β-unsaturated aldehydes under water-gas shift conditions

Tlili, Anis,Schranck, Johannes,Neumann, Helfried,Beller, Matthias

, p. 15935 - 15939 (2012)

Iron-catalyzed reductions: Selective iron-catalyzed reduction of aldehydes with hydrogen generated in situ by the water-gas shift reaction is presented (see scheme). The generality and selectivity of this mild procedure are demonstrated by the efficient reduction of various aromatic, aliphatic and α,β-unsaturated aldehydes.

Iron-based catalysts for the hydrogenation of esters to alcohols

Chakraborty, Sumit,Dai, Huiguang,Bhattacharya, Papri,Fairweather, Neil T.,Gibson, Michael S.,Krause, Jeanette A.,Guan, Hairong

, p. 7869 - 7872 (2014)

Hydrogenation of esters is vital to the chemical industry for the production of alcohols, especially fatty alcohols that find broad applications in consumer products. Current technologies for ester hydrogenation rely on either heterogeneous catalysts operating under extreme temperatures and pressures or homogeneous catalysts containing precious metals such as ruthenium and osmium. Here, we report the hydrogenation of esters under relatively mild conditions by employing an iron-based catalyst bearing a PNP-pincer ligand. This catalytic system is also effective for the conversion of coconut oil derived fatty acid methyl esters to detergent alcohols without adding any solvent.

The use of - for the carbonylation of primary, secondary and allylic halides

Davies, Stephen G.,Smallridge, Andrew J.,Ibbotson, Arthur

, p. 195 - 201 (1990)

The tricarbonyl nitrosyl ferrate anion (1) is an efficient carbonylation reagent for the formation of methyl esters from primary and secondary alkyl and benzyl halides.The carbonylation of allyl halides results in the exclusive formation of β,γ-unsaturated esters.Studies of the catalytic use of 1 are also described.

A convenient and general iron-catalyzed hydrosilylation of aldehydes

Shaikh, Nadim S.,Junge, Kathrin,Beller, Matthias

, p. 5429 - 5432 (2007)

A general and highly chemoselective hydrosilylation of aldehydes using iron catalysts is reported. Fe(OAc)2 in the presence of tricyclohexylphosphine as ligand and polymethylhydrosiloxane (PMHS) as an economical hydride source forms an efficient catalyst system for the hydrosilylation of a variety of aldehydes. Aryl, heteroaryl, alkyl and α,β-unsaturated aldehydes are successfully reduced to the corresponding primary alcohols. Broad substrate scope and high tolerance against several functional groups make the process synthetically useful.

Reduction of Some Functional Groups with Titanium(IV) Chloride/Sodium Borohydride

Kano, Shinzo,Tanaka, Yasuyuki,Sugino, Eiichi,Hibino, Sstoshi

, p. 695 - 697 (1980)

-

Rate acceleration in nucleophilic alkylation of carbonyl compounds with a new template containing two metallic centers

Ooi, Takashi,Takahashi, Makoto,Maruoka, Keiji

, p. 835 - 837 (1998)

Two aluminum centers aligned in the same direction capture carbonyl groups in such a way that efficient alkyl transfer becomes possible from aluminum to the carbon atom. This occurs via a favorable cyclic six-membered transition state (a). Carbonyl compounds can now be alkylated with otherwise less reactive alkylmetal species.

Improved Second Generation Iron Pincer Complexes for Effective Ester Hydrogenation

Elangovan, Saravanakumar,Wendt, Bianca,Topf, Christoph,Bachmann, Stephan,Scalone, Michelangelo,Spannenberg, Anke,Jiao, Haijun,Baumann, Wolfgang,Junge, Kathrin,Beller, Matthias

, p. 820 - 825 (2016)

Hydrogenation of esters to alcohols with a well-defined iron iPr2PNP pincer complex has been recently reported by us and other groups. We now introduce a novel and sterically less hindered Et2PNP congener that provides superior catalytic activity in the hydrogenation of various carboxylic acid esters and lactones compared to the known complex. Successful hydrogenation proceeds under relatively mild conditions (60°C) with lower catalyst loadings.

Palladium doping of In2O3 towards a general and selective catalytic hydrogenation of amides to amines and alcohols

Sorribes, Iván,Lemos, Samantha C. S.,Martín, Santiago,Mayoral, Alvaro,Lima, Renata C.,Andrés, Juan

, p. 6965 - 6976 (2019)

Herein, the first general heterogeneous catalytic protocol for the hydrogenation of primary, secondary and tertiary amides to their corresponding amines and alcohols is described. Advantageously, this catalytic protocol works under additive-free conditions and is compatible with the presence of aromatic rings, which are fully retained in the final products. This hydrogenative C-N bond cleavage methodology is catalyzed by a Pd-doped In2O3 catalyst prepared by a microwave hydrothermal-assisted method followed by calcination. This catalyst displays highly dispersed Pd2+ ionic species in the oxide matrix of In2O3 that have appeared to be essential for its high catalytic performance.

Bridged bicyclic 2,3-dioxabicyclo[3.3.1]nonanes as antiplasmodial agents: Synthesis, structure-activity relationships and studies on their biomimetic reaction with Fe(II)

D'Alessandro, Sarah,Alfano, Gloria,Di Cerbo, Luisa,Brogi, Simone,Chemi, Giulia,Relitti, Nicola,Brindisi, Margherita,Lamponi, Stefania,Novellino, Ettore,Campiani, Giuseppe,Gemma, Sandra,Basilico, Nicoletta,Taramelli, Donatella,Baratto, Maria Camilla,Pogni, Rebecca,Butini, Stefania

, (2019)

Despite recent advancements in its control, malaria is still a deadly parasitic disease killing millions of people each year. Progresses in combating the infection have been made by using the so-called artemisinin combination therapies (ACTs). Natural and synthetic peroxides are an important class of antimalarials. Here we describe a new series of peroxides synthesized through a new elaboration of the scaffold of bicyclic-fused/bridged synthetic endoperoxides previously developed by us. These peroxides are produced by a straightforward synthetic protocol and are characterized by submicromolar potency when tested against both chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains. To investigate their mode of action, the biomimetic reaction of the representative compound 6w with Fe(II) was studied by EPR and the reaction products were characterized by NMR. Rationalization of the observed structure-activity relationship studies was performed by molecular docking. Taken together, our data robustly support the hypothesized mode of activation of peroxides 6a-cc and led to the definition of the key structural requirements responsible for the antiplasmodial potency. These data will pave the way in future to the rational design of novel optimized antimalarials suitable for in vivo investigation.

Unexpected CNN-to-CC Ligand Rearrangement in Pincer-Ruthenium Precatalysts Leads to a Base-Free Catalyst for Ester Hydrogenation

Le, Linh,Liu, Jiachen,He, Tianyi,Malek, Jack C.,Cervarich, Tia N.,Buttner, John C.,Pham, John,Keith, Jason M.,Chianese, Anthony R.

, (2019)

We report the conversion of a series of CNN-pincer-ruthenium complexes Ru(CNN)HCl(CO) to a CC-chelated form Ru(CC)(PR3)2H(CO) on reaction with sodium tert-butoxide and monodentate phosphines. When the phosphine is triphenylphosphine, cis-phosphine complexes form at room temperature, which convert to the trans isomer at elevated temperatures. When the phosphine is tricyclohexylphosphine, only the trans-phosphine isomer is observed. The CC-chelated complexes are active catalysts for the hydrogenation of esters, without the need for added base. The ligand structure-activity relationship in the series of CC-chelated complexes mirrors that in the precursor CNN-Ru complexes, potentially indicating a common catalytic mechanism. Density functional theory calculations establish a plausible mechanism for the CNN-to-CC rearrangement and demonstrate that this rearrangement is potentially reversible under the conditions of ester hydrogenation catalysis.

Homologation of representative boronic esters using in situ generated (halomethyl)lithiums: A comparative study

Soundararajan, Raman,Li, Guisheng,Brown, Herbert C.

, p. 8957 - 8960 (1994)

A comparative study of the homologation of representative boronic esters with in situ generated LiCH2X (X = Cl; Br; I) is presented wherein the reactivity differences arising out of the steric and electronic effects of the migrating groups, and the nature of the ester groups are determined and discussed.

Selective hydrogenation of aromatic compounds using modified iridium nanoparticles

Jiang, He-Yan,Xu, Jie,Sun, Bin

, (2018)

Till now, Ionic liquid-stabilized metal nanoparticles were investigated as catalytic materials, mostly in the hydrogenation of simple substrates like olefins or arenes. The adjustable hydrogenation products of aromatic compounds, including quinoline and relevant compounds, aromatic nitro compounds, aromatic ketones as well as aromatic aldehydes, are always of special interest, since they provide more choices for additional derivatization. Iridium nanoparticles (Ir NPs) were synthesized by the H2 reduction in imidazolium ionic liquid. TEM indicated that the Ir NPs is worm-like shape with the diameter around 12.2?nm and IR confirmed the modification of phosphine-functionalized ionic liquids (PFILs) to the Ir NPs. With the variation of the modifier, solvent and reaction temperature, substrate like quinoline and relevant compounds, aromatic nitro compounds, aromatic ketones as well as aromatic aldehydes could be hydrogenated by Ir NPs with interesting adjustable catalytic activity and chemoselectivity. Ir NPs modified by PFILs are simple and efficient catalysts in challenging chemoselective hydrogenation of quinoline and relevant compounds, aromatic nitro compounds, aromatic ketones as well as aromatic aldehydes. The activity and chemoselectivity of the Ir NPs could be obviously impacted or adjusted by altering the modifier, solvent and reaction temperature.

Selective hydrogenation of amides using Rh/Mo catalysts

Beamson, Graham,Papworth, Adam J.,Philipps, Charles,Smith, Andrew M.,Whyman, Robin

, p. 93 - 102 (2010)

Rh/Mo catalysts formed in situ from Rh6(CO)16 and Mo(CO)6 are effective for the liquid phase hydrogenation of CyCONH2 to CyCH2NH2 in up to 87% selectivity, without the requirement for ammonia to inhibit secondary amine formation. Use of in situ HP-FTIR spectroscopy has shown that decomposition of metal carbonyl precursors occurs during an extended induction period, with the generation of recyclable, heterogeneous, bimetallic catalysts. Variations in Mo:Rh content have revealed significant synergistic effects on catalysis, with optimum performance at values of ca. 0.6, and substantially reduced selectivities at ≥1. Good amide conversions are noted within the reaction condition regimes 50-100 bar H2 and 130-160 °C. Ex situ characterization of the catalysts, using XRD, XPS and EDX-STEM, has provided evidence for intimately mixed (ca. 2-4 nm) particles that contain metallic Rh and reduced Mo oxides, together with MoO3. Silica-supported Rh/Mo analogues, although active, perform poorly at 150 °C and deactivate during recycle.

Selective hydrogenation of primary amides and cyclic di-peptides under Ru-catalysis

Subaramanian, Murugan,Sivakumar, Ganesan,Babu, Jessin K.,Balaraman, Ekambaram

, p. 12411 - 12414 (2020)

A ruthenium(II)-catalyzed selective hydrogenation of challenging primary amides and cyclic di-peptides to their corresponding primary alcohols and amino alcohols, respectively, is reported. The hydrogenation reaction operates under mild and eco-benign conditions and can be scaled-up.

Rhodium nanoparticles entrapped in boehmite nanofibers: Recyclable catalyst for arene hydrogenation under mild conditions

Park, In Soo,Kwon, Min Serk,Kim, Namdu,Lee, Jae Sung,Kang, Kyung Yeon,Park, Jaiwook

, p. 5667 - 5669 (2005)

A new recyclable rhodium catalyst was synthesized by a simple procedure from readily available reagents, which showed high activities in the hydrogenation of various arenes under 1 atm H2 at room temperature. The Royal Society of Chemistry 2005.

Alkane oxidation with peroxides catalyzed by cage-like copper(II) silsesquioxanes

Vinogradov, Mikhail M.,Kozlov, Yuriy N.,Bilyachenko, Alexey N.,Nesterov, Dmytro S.,Shul'pina, Lidia S.,Zubavichus, Yan V.,Pombeiro, Armando J. L.,Levitsky, Mikhail M.,Yalymov, Alexey I.,Shul'pin, Georgiy B.

, p. 187 - 199 (2015)

Isomeric cage-like tetracopper(II) silsesquioxane complexes [(PhSiO1.5)12(CuO)4(NaO0.5)4] (1a), [(PhSiO1.5)6(CuO)4(NaO0.5)4(PhSiO1.5)6] (1b) and binuclear complex [(PhSiO1.5)10(CuO)2(NaO0.5)2] (2) have been studied by various methods. These compounds can be considered as models of some multinuclear copper-containing enzymes. Compounds 1a and 2 are good pre-catalysts for the alkane oxygenation with hydrogen peroxide in air in an acetonitrile solution. Thus, the 1a-catalyzed reaction with cyclohexane at 60°C gave mainly cyclohexyl hydroperoxide in 17% yield (turnover number, TON, was 190 after 230 min and initial turnover frequency, TOF, was 100 h-1). The alkyl hydroperoxide partly decomposes in the course of the reaction to afford the corresponding ketone and alcohol. The effective activation energy for the cyclohexane oxygenation catalyzed by compounds 1a and 2 is 16 ± 2 and 17 ± 2 kcal mol-1, respectively. Selectivity parameters measured in the oxidation of linear and branched alkanes and the kinetic analysis revealed that the oxidizing species in the reaction is the hydroxyl radical. The analysis of the dependence of the initial reaction rate on the initial concentration of cyclohexane led to a conclusion that hydroxyl radicals attack the cyclohexane molecules in proximity to the copper reaction centers. The oxidations of saturated hydrocarbons with tert-butylhydroperoxide (TBHP) catalyzed by complexes 1a and 2 exhibit unusual selectivity parameters which are due to the steric hindrance created by bulky silsesquioxane ligands surrounding copper reactive centers. Thus, the methylene groups in n-octane have different reactivities: the regioselectivity parameter for the oxidation with TBHP catalyzed by 1a is 1:10.5:8:7. Furthermore, in the oxidation of methylcyclohexane the position 2 relative to the methyl group of this substrate is noticeably less reactive than the corresponding positions 3 and 4. Finally, the oxidation of trans-1,2-dimethylcyclohexane with TBHP catalyzed by complexes 1a and 2 proceeds stereoselectively with the inversion of configuration. The 1a-catalyzed reaction of cyclohexane with H216O2 in an atmosphere of 18O2 gives cyclohexyl hydroperoxide containing up to 50% of 18O. The small amount of cyclohexanone, produced along with cyclohexyl hydroperoxide, is 18O-free and is generated apparently via a mechanism which does not include hydroxyl radicals and incorporation of molecular oxygen from the atmosphere.

-

Smith,Brown

, p. 6135 (1952)

-

Iron-catalyzed chemoselective hydride transfer reactions

Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc

supporting information, (2021/06/07)

A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.

Ambient-pressure highly active hydrogenation of ketones and aldehydes catalyzed by a metal-ligand bifunctional iridium catalyst under base-free conditions in water

Wang, Rongzhou,Yue, Yuancheng,Qi, Jipeng,Liu, Shiyuan,Song, Ao,Zhuo, Shuping,Xing, Ling-Bao

, p. 1 - 7 (2021/05/17)

A green, efficient, and high active catalytic system for the hydrogenation of ketones and aldehydes to produce corresponding alcohols under atmospheric-pressure H2 gas and ambient temperature conditions was developed by a water-soluble metal–ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(OH)][Na] in water without addition of a base. The catalyst exhibited high activity for the hydrogenation of ketones and aldehydes. Furthermore, it was worth noting that many readily reducible or labile functional groups in the same molecule, such as cyan, nitro, and ester groups, remained unchanged. Interestingly, the unsaturated aldehydes can be also selectively hydrogenated to give corresponding unsaturated alcohols with remaining C=C bond in good yields. In addition, this reaction could be extended to gram levels and has a large potential of wide application in future industrial.

Radical Chain Reduction via Carbon Dioxide Radical Anion (CO2?-)

Hendy, Cecilia M.,Jui, Nathan T.,Lian, Tianquan,Smith, Gavin C.,Xu, Zihao

supporting information, p. 8987 - 8992 (2021/07/01)

We developed an effective method for reductive radical formation that utilizes the radical anion of carbon dioxide (CO2?-) as a powerful single electron reductant. Through a polarity matched hydrogen atom transfer (HAT) between an electrophilic radical and a formate salt, CO2?- formation occurs as a key element in a new radical chain reaction. Here, radical chain initiation can be performed through photochemical or thermal means, and we illustrate the ability of this approach to accomplish reductive activation of a range of substrate classes. Specifically, we employed this strategy in the intermolecular hydroarylation of unactivated alkenes with (hetero)aryl chlorides/bromides, radical deamination of arylammonium salts, aliphatic ketyl radical formation, and sulfonamide cleavage. We show that the reactivity of CO2?- with electron-poor olefins results in either single electron reduction or alkene hydrocarboxylation, where substrate reduction potentials can be utilized to predict reaction outcome.

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