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103-65-1 Usage

General Description

1-Phenylpropane, also known as ethylbenzene, is a chemical compound with the molecular formula C8H10. It is a simple aromatic hydrocarbon consisting of a phenyl group (C6H5) attached to a propane chain (C3H7). Ethylbenzene is a colorless liquid with a sweet, gasoline-like odor and is considered one of the key chemicals in the production of styrene, a fundamental compound in the plastics industry.

Check Digit Verification of cas no

The CAS Registry Mumber 103-65-1 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 3 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 103-65:
(5*1)+(4*0)+(3*3)+(2*6)+(1*5)=31
31 % 10 = 1
So 103-65-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H12/c1-2-6-9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3

103-65-1 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Alfa Aesar

  • (B21468)  n-Propylbenzene, 98%   

  • 103-65-1

  • 100g

  • 358.0CNY

  • Detail
  • Alfa Aesar

  • (B21468)  n-Propylbenzene, 98%   

  • 103-65-1

  • 500g

  • 1496.0CNY

  • Detail
  • Sigma-Aldrich

  • (82118)  Propylbenzene  analytical standard

  • 103-65-1

  • 82118-5ML

  • 616.59CNY

  • Detail
  • Sigma-Aldrich

  • (82118)  Propylbenzene  analytical standard

  • 103-65-1

  • 82118-10ML

  • 1,107.99CNY

  • Detail
  • Aldrich

  • (82119)  Propylbenzene  ≥99.0% (GC)

  • 103-65-1

  • 82119-25ML

  • 644.67CNY

  • Detail
  • Aldrich

  • (82119)  Propylbenzene  ≥99.0% (GC)

  • 103-65-1

  • 82119-100ML

  • 2,400.84CNY

  • Detail
  • Aldrich

  • (P52407)  Propylbenzene  98%

  • 103-65-1

  • P52407-25ML

  • 228.15CNY

  • Detail
  • Aldrich

  • (P52407)  Propylbenzene  98%

  • 103-65-1

  • P52407-100ML

  • 545.22CNY

  • Detail
  • Aldrich

  • (P52407)  Propylbenzene  98%

  • 103-65-1

  • P52407-500ML

  • 1,807.65CNY

  • Detail

103-65-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name propylbenzene

1.2 Other means of identification

Product number -
Other names N-PROPYLBENZENE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fuels and fuel additives,Intermediates,Solvents (which become part of product formulation or mixture)
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:103-65-1 SDS

103-65-1Synthetic route

allylbenzene
300-57-2

allylbenzene

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With Pt-Sn-citrate; hydrogen In methanol at 50℃; under 3800 Torr; for 3h; var. temperatures; var. pressures;100%
With Pt-Sn-citrate; hydrogen In methanol at 50℃; under 3800 Torr; for 3h;100%
With C49H60BF2IrN5(1+)*C32H12BF24(1-); hydrogen In 1,2-dichloro-ethane at 20℃; for 0.166667h; Reagent/catalyst; Schlenk technique;100%
1-phenylpropene
637-50-3

1-phenylpropene

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With C28H18Co(1-)*K(1+)*2C4H10O2; hydrogen In toluene at 60℃; under 1500.15 Torr; for 24h; Temperature; Time; Reagent/catalyst; chemoselective reaction;100%
With iron(III) chloride; lithium aluminium tetrahydride; hydrogen In tetrahydrofuran at 18℃; under 750.075 Torr; for 20h; Inert atmosphere; Sealed tube;100%
In methanol for 0.5h; UV-irradiation;99%
1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With hydrogen In ethanol at 39.84℃; under 760.051 Torr; for 5h;100%
With hydrogen In 1,4-dioxane at 200℃; under 15001.5 Torr;95.8%
Stage #1: 1-phenyl-propan-1-one With iron(III) chloride In methanol at 20℃; for 0.05h;
Stage #2: In methanol at 20℃; for 0.166667h; chemoselective reaction;
91%
1-propenylbenzene
873-66-5

1-propenylbenzene

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With hydrogen; sodium triethylborohydride In tetrahydrofuran under 30003 Torr; for 20h; Catalytic behavior; Inert atmosphere;100%
With water; zinc; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane at 90℃; for 20h;99%
With [Fe(nacnac)dippCH2SiMe3]; N-butylamine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 20℃; for 16h; Sealed tube; Schlenk technique; Glovebox; Inert atmosphere;99%
1,1,3,3-Tetramethyldisiloxane
3277-26-7

1,1,3,3-Tetramethyldisiloxane

2-phenoxy-1-phenylpropane-1, 3-diol
70110-65-5

2-phenoxy-1-phenylpropane-1, 3-diol

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate; water In dichloromethane at 20℃; for 16h; Inert atmosphere;100%
1-Phenyl-1-propanol
93-54-9

1-Phenyl-1-propanol

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With chloro-trimethyl-silane; acetonitrile; sodium iodide In hexane for 24h; Ambient temperature;99%
With chloro-trimethyl-silane; acetonitrile; sodium iodide In hexane for 24h; Ambient temperature;99%
With hydrogen In ethanol at 80℃; under 2250.23 Torr; for 3h; Catalytic behavior; Temperature; Solvent; Inert atmosphere;94%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With LiCrH4*2LiCl*2THF In tetrahydrofuran at 25℃; for 12h;99%
With indium(III) chloride; sodium tetrahydroborate In acetonitrile at 20℃; for 2h;95%
With sodium tetrahydroborate; water In methanol at 20℃; for 0.5h;87%
(η5-C5H5)Fe(CO)2CH2CH2C6H5

(η5-C5H5)Fe(CO)2CH2CH2C6H5

trimethylsilan
993-07-7

trimethylsilan

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

C5H5Fe(CO)H(Si(CH3)3)2

C5H5Fe(CO)H(Si(CH3)3)2

C

C5H5Fe(CO)4

C5H5Fe(CO)4

D

Propylbenzene
103-65-1

Propylbenzene

E

trimethyl(3-phenylpropoxy)silane
14629-60-8

trimethyl(3-phenylpropoxy)silane

Conditions
ConditionsYield
In benzene-d6 react. of Fe complex and HSiMe3 in benzene, 90°C, 9 h; yields detd. by (1)H-NMR (C5H5Fe(CO)H(SiMe3)2; elem. anal.) and GL-chromy. (other products);A 0%
B 91%
C 10%
D 0%
E 98%
1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

A

cis-1-phenyl-1-propylene
766-90-5

cis-1-phenyl-1-propylene

B

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With hydrogen In methanol at 30℃; under 760.051 Torr; for 2h;A 97%
B 3%
With hydrogen; poly(amidoamine) dendron-stabilised Pd(0) nanoparticle In dichloromethane at 25℃; under 760.051 Torr; for 1h;A 96%
B 4%
With hydrogen; Et4N In 1,2-dimethoxyethane at 100℃; under 38000 Torr; for 18h; Product distribution; further unsaturated compounds of different types;A 8%
B 90%
bis(3-phenylpropyl) selenide

bis(3-phenylpropyl) selenide

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 67℃; Irradiation;97%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With palladium dichloride In methanol at 40℃; for 18h; Inert atmosphere; Green chemistry; chemoselective reaction;96%
With [IrCl(CO)(PPh3)2]; hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Wolff-Kishner Reduction; Sealed tube;81%
With [IrCl(CO)(PPh3)2]; hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Sealed tube;81%
1-(4-chlorophenyl)-1-propanol
13856-85-4

1-(4-chlorophenyl)-1-propanol

A

Propylbenzene
103-65-1

Propylbenzene

B

1-Phenyl-1-propanol
93-54-9

1-Phenyl-1-propanol

Conditions
ConditionsYield
With potassium hydroxide; hydrogen; Aliquat 336; palladium on activated charcoal In 2,2,4-trimethylpentane at 50℃; for 0.833333h; Product distribution; various time, solvents; also in the presence of various aromatic halides as promoters; further benzylic alcohols;A 96%
B 4%
(cp)Fe(CO)2(COCH2CH2Ph)

(cp)Fe(CO)2(COCH2CH2Ph)

trimethylstannane
1631-73-8

trimethylstannane

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

C5H5Fe(CO)H(Sn(CH3)3)2

C5H5Fe(CO)H(Sn(CH3)3)2

C

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

D

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
In benzene-d6 react. of Fe complex and HSnMe3 in benzene, 120°C, 7 h; yields detd. by (1)H-NMR (C5H5Fe(CO)H(SnMe3)2; elem. anal.) and GL-chromy. (other products);A <3
B 73%
C 96%
D 0%
In benzene-d6 Irradiation (UV/VIS); irradn. of Fe complex and HSnMe3 in benzene for 6 h; yields detd. by (1)H-NMR and GL-chromy.;A 79%
B 82%
C 0%
D 0%
1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With tetrahydroxydiboron; palladium 10% on activated carbon; water In dichloromethane at 20℃; for 5h; Inert atmosphere;95%
With 2C2H3O2(1-)*Pd(2+)*3Na(1+)*C18H12O9PS3(3-); hydrogen; glycerol at 100℃; under 2250.23 Torr; for 2h; Schlenk technique;92%
With hydrogen; palladium on activated charcoal In hexane under 1520 Torr; Thermodynamic data; ΔH;
N-benzyl-2-phenylethylamine
3647-71-0

N-benzyl-2-phenylethylamine

triethylaluminum
97-93-8

triethylaluminum

A

Propylbenzene
103-65-1

Propylbenzene

B

phenethylamine
64-04-0

phenethylamine

C

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

D

toluene
108-88-3

toluene

Conditions
ConditionsYield
In benzene for 38h; Irradiation;A 50%
B 95%
C n/a
D 14%
propyl bromide
106-94-5

propyl bromide

triphenylphosphine
603-35-0

triphenylphosphine

A

Propylbenzene
103-65-1

Propylbenzene

B

diphenylphosphinopropane
7650-84-2

diphenylphosphinopropane

Conditions
ConditionsYield
Stage #1: triphenylphosphine With lithium In diethyl ether at 20℃; for 3h; Inert atmosphere;
Stage #2: propyl bromide In diethyl ether at 0 - 30℃; for 2.5h;
A 94.8%
B 92.4%
Stage #1: triphenylphosphine With lithium In diethyl ether at 20℃; for 3h; Inert atmosphere;
Stage #2: propyl bromide In diethyl ether at 0 - 30℃; for 1.5h; Inert atmosphere;
3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃;94%
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 20h;94%
With 1,1,3,3-Tetramethyldisiloxane; tris(pentafluorophenyl)borate In benzene-d6 at 23℃; for 1h; Glovebox; Schlenk technique;100 %Spectr.
(η5-C5H5)Fe(CO)2CH2CH2C6H5

(η5-C5H5)Fe(CO)2CH2CH2C6H5

trimethylstannane
1631-73-8

trimethylstannane

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

C5H5Fe(CO)H(Sn(CH3)3)2

C5H5Fe(CO)H(Sn(CH3)3)2

C

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

D

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
In benzene-d6 react. of Fe complex and HSnMe3 in benzene, 60°C, 13 h; yields detd. by (1)H-NMR (C5H5Fe(CO)H(SnMe3)2; elem. anal.) and GL-chromy. (other products);A 0%
B 88%
C 94%
D <3
In benzene-d6 Irradiation (UV/VIS); irradn. of Fe complex and HSnMe3 in benzene for 7 h; yields detd. by (1)H-NMR and GL-chromy.;A 0%
B 85%
C <3
D 86%
1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

A

1-propenylbenzene
873-66-5

1-propenylbenzene

B

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With C41H38BFeN3P2; hydrogen In tetrahydrofuran at 20 - 90℃; under 7500.75 Torr; for 27h; Inert atmosphere;A 94%
B 11%
With formic acid; para-xylene; 1,3-bis(2,4,6-trimethylphenyl)-3,4,5,6-tetrahydro-pyrimidin-1-ium palladium (divinyltetramethyldisiloxane); triethylamine In acetonitrile at 80℃; for 2h; Catalytic behavior; Inert atmosphere; Schlenk technique; Reflux; chemoselective reaction;
With C42H44ClN4P2Ru(1+)*Cl(1-); potassium tert-butylate; isopropyl alcohol at 80℃; for 72h; Schlenk technique; Inert atmosphere;A n/a
B 77 %Spectr.
With hydrogen; iron(II) acetate; diisobutylaluminium hydride In tetrahydrofuran; toluene at 30℃; under 1500.15 Torr; for 3h; stereoselective reaction;A n/a
B n/a
1-Chloropropane
540-54-5

1-Chloropropane

triphenylphosphine
603-35-0

triphenylphosphine

A

Propylbenzene
103-65-1

Propylbenzene

B

diphenylphosphinopropane
7650-84-2

diphenylphosphinopropane

Conditions
ConditionsYield
Stage #1: triphenylphosphine With lithium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: 1-Chloropropane In tetrahydrofuran at 5 - 50℃; for 6.25h;
A 93.5%
B 91.6%
Cinnamyl acetate
21040-45-9

Cinnamyl acetate

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In methanol at -20℃; for 0.5h;93%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); polystyrene-supported organotin catalyst In N,N-dimethyl acetamide at 80℃; for 6.5h;93%
With indium(III) chloride; sodium tetrahydroborate In acetonitrile at 20℃; for 2h;90%
With triethylsilane; indium(III) chloride; triethyl borane In hexane; dichloromethane at 20℃; for 2h;83%
Multi-step reaction with 2 steps
1: tetrahydrofuran / 0.5 h / 20 °C / Glovebox; Sealed tube; Irradiation
2: sodium methylate / 12 h / 20 °C / Glovebox; Sealed tube; Irradiation
View Scheme
cis-1-phenyl-1-propylene
766-90-5

cis-1-phenyl-1-propylene

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With hydrogen; sodium triethylborohydride In tetrahydrofuran at 23℃; under 30003 Torr; for 20h; Reagent/catalyst; Autoclave;92%
With hydrogen; sodium triethylborohydride In tetrahydrofuran at 23℃; under 30402 Torr; for 70h; Catalytic behavior; Inert atmosphere; Schlenk technique;36%
With hydrogen; sodium triethylborohydride In tetrahydrofuran at 23℃; under 30402 Torr; for 18h; Reagent/catalyst; Glovebox; Inert atmosphere;12%
5-[3-Phenyl(1,1-(2)H2)prop-2-enyloxy]-1-phenyltetrazole

5-[3-Phenyl(1,1-(2)H2)prop-2-enyloxy]-1-phenyltetrazole

A

5-phenyl-1H-tetrazolone
5097-82-5

5-phenyl-1H-tetrazolone

B

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With formic acid; palladium on activated charcoal In ethanol; benzene for 0.166667h; Heating; Yields of byproduct given;A n/a
B 92%
With formic acid; palladium on activated charcoal In ethanol; benzene for 0.0833333h; Heating; Yield given. Yields of byproduct given;
cinnamyl chloride
2687-12-9

cinnamyl chloride

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; water In methanol at 20℃; for 0.166667h;92%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at -78 - 67℃;91%
(η5-C5H5)Fe(CO)(PPh3)(C(O)CH2CH2Ph)

(η5-C5H5)Fe(CO)(PPh3)(C(O)CH2CH2Ph)

trimethylstannane
1631-73-8

trimethylstannane

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

C5H5Fe(CO)H(Sn(CH3)3)2

C5H5Fe(CO)H(Sn(CH3)3)2

C

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

D

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
In benzene-d6 react. of Fe complex and HSnMe3 in benzene, 120°C, 6 h; yields detd. by (1)H-NMR and GL-chromy.;A <3
B 91%
C 91%
D <3
In benzene-d6 Irradiation (UV/VIS); irradn. of Fe complex and HSnMe3 in benzene for 24 h; yields detd. by (1)H-NMR and GL-chromy.;A 0%
B 0%
C <3
D 37%
3-phenylprop-2-en-1-yl bromide
4392-24-9

3-phenylprop-2-en-1-yl bromide

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; water In methanol at 20℃; for 0.25h;91%
1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

A

Propylbenzene
103-65-1

Propylbenzene

B

1-Phenyl-1-propanol
93-54-9

1-Phenyl-1-propanol

Conditions
ConditionsYield
With sodium tetrahydroborate; aluminium trichloride In tetrahydrofuran for 2h; Heating;A 90%
B 7 % Chromat.
With sodium tetrahydroborate; aluminium trichloride In tetrahydrofuran for 2h; Ambient temperature; Yield given. Yields of byproduct given;
With hydrogen In toluene at 80℃; under 15001.5 Torr; for 24h; Autoclave; chemoselective reaction;
With hydrogen In tetrahydrofuran at 50℃; under 15001.5 Torr; for 24h; Autoclave; chemoselective reaction;
Propylbenzene
103-65-1

Propylbenzene

propylcyclohexane
1678-92-8

propylcyclohexane

Conditions
ConditionsYield
With Ti8O8(14+)*6C8H4O4(2-)*4O(2-)*3.3Li(1+)*0.7Co(2+)*0.7C4H8O*0.7H(1-); hydrogen In neat (no solvent) at 120℃; under 37503.8 Torr; for 18h;100%
With nickel at 220 - 240℃; under 73550.8 Torr; Hydrogenation;
With platinum(IV) oxide; acetic acid Hydrogenation;
Propylbenzene
103-65-1

Propylbenzene

4-(methoxymethoxy)-4'-methoxybenzophenone
115499-97-3

4-(methoxymethoxy)-4'-methoxybenzophenone

1-(4-methoxymethoxyphenyl)-1-(4-methoxyphenyl)-2-phenylbutan-1-ol
671791-56-3

1-(4-methoxymethoxyphenyl)-1-(4-methoxyphenyl)-2-phenylbutan-1-ol

Conditions
ConditionsYield
Stage #1: phenylpropane With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate In tetrahydrofuran; hexane at 20℃; for 0.5h;
Stage #2: 4-(methoxymethoxy)-4'-methoxybenzophenone In tetrahydrofuran; hexane at -78 - 20℃; for 4.5h;
97%
Stage #1: phenylpropane With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate
Stage #2: 4-(methoxymethoxy)-4'-methoxybenzophenone
97%
Propylbenzene
103-65-1

Propylbenzene

2,4-dinitro-1-propylbenzene
24503-35-3

2,4-dinitro-1-propylbenzene

Conditions
ConditionsYield
With nitric acid; Chloroacetic anhydride at 50℃; for 4h;96%
With sulfuric acid; nitric acid at 0 - 20℃;89%
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid at 0 - 20℃; for 0.5h;
2-Iodobenzoic acid
88-67-5

2-Iodobenzoic acid

Propylbenzene
103-65-1

Propylbenzene

1-(4-propylphenyl)-1H-1λ3-benzo[b]iodo-3(2H)-one
1427465-30-2

1-(4-propylphenyl)-1H-1λ3-benzo[b]iodo-3(2H)-one

Conditions
ConditionsYield
Stage #1: 2-Iodobenzoic acid With Oxone; sulfuric acid at 5 - 20℃; for 0.5h;
Stage #2: phenylpropane In dichloromethane at 5 - 20℃; for 3h;
94%
Propylbenzene
103-65-1

Propylbenzene

1-Phenyl-1-propanol
93-54-9

1-Phenyl-1-propanol

Conditions
ConditionsYield
With C20H24B10Cl4FeN6; dihydrogen peroxide In methanol at 20℃; for 6h;93%
With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); oxygen Kinetics; relative chain propagation rates;
With NADPH In dimethyl sulfoxide at 30℃; pH=7.4; Product distribution; Further Variations:; Reagents;99 % Chromat.
Propylbenzene
103-65-1

Propylbenzene

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

Conditions
ConditionsYield
With potassium permanganate; Rexyn 101 H ion exchange resin In dichloromethane for 5.45h; Heating;93%
With potassium permanganate on Zeolite beta In 1,2-dichloro-ethane for 96h; Ambient temperature;92%
With sodium bromate; sulfuric acid; silica gel at 20℃; for 3h;92%
Propylbenzene
103-65-1

Propylbenzene

2-bromo-1-phenyl-1-propanone
2114-00-3

2-bromo-1-phenyl-1-propanone

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water In ethyl acetate at 60℃; for 6h; Wohl-Ziegler Bromination;93%
With hydrogen bromide; oxygen In water; ethyl acetate at 20℃; for 10h; Irradiation;61%

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The evaluation of using 1-butyl-3-methylimidazolium hexaflurophosphate ionic liquid, [bmim][PF6], as a solvent for the extraction of propylbenzene from aliphatic compounds was studied. The (liquid + liquid) equilibrium (LLE) for two ternary systems comprising {dodecane or tetradecane + propylben...detailed

Soot formation of dodecane, aviation bio-paraffins and their blends with Propylbenzene (cas 103-65-1) in diffusion flames08/11/2019

Co-annular smoke-free laminar diffusion wick-fed flames of dodecane, aviation bio-paraffins and each blended with various amounts of propylbenzene of 10, 20, 25 vol% have been used to study soot formation. A light extinction method is adopted to determine the total soot volume (TSV) as a functio...detailed

103-65-1Relevant articles and documents

ZUR BILDUNGSWEISE VON 1-PHENYLPROPYLLITHIUM AUS BENZYLLITHIUM UND ETHYLEN IN TETRAHYDROFURAN

Maercker, Adalbert,Stoetzel, Reinhard

, p. 1 - 12 (1983)

3-Phenylpropyllithium primarily formed by the addition of benzyllithium to ethylene in THF does not undergo an intramolecular 1,3-proton shift to 1-phenylpropyllithium.Fast protonation by the solvent takes place instead, yielding n-propylbenzene and new ethylene.An equilibrium is then established between n-propylbenzene and additional benzyllithium, with the formation of toluene and 1-phenylpropyllithium; the equilibrium, however, strongly favours the starting materials (K293=1.1*10-4).As, on the other hand, 1-phenylpropyllithium reacts with ethylene much more rapidly than does benzyllithium, it is removed from the equilibrium and mainly branched secondary products are still obtained.

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Ipatieff,Pines,Schmerling

, p. 253,259 (1940)

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Salt-free preparation of trimethylsilyl ethers by B(C6F 5)3-catalyzed transfer silylation by using a Me 3SiH surrogate

Simonneau, Antoine,Friebel, Jonas,Oestreich, Martin

, p. 2077 - 2083 (2014)

An unprecedented transfer silylation of alcohols catalyzed by the strong Lewis acid B(C6F5)3 is described. Gaseous Me3SiH is released in situ by B(C6F5) 3-catalyzed decomposition of 3-trimethylsilylcyclohexa-1,4-diene and subsequently reacts with an alcohol in a dehydrogenative Si-O coupling promoted by the same boron catalyst. Benzene and dihydrogen are formed during the reaction, but no salt waste is. This expedient protocol is applicable to several silicon groups, and the preparation of trimethylsilyl ethers presented here is potentially useful for alcohol derivatization prior to GLC analysis. Copyright

Distribution of Metal Cations in Ni-Mo-W Sulfide Catalysts

Hein, Jennifer,Gutiérrez, Oliver Y.,Schachtl, Eva,Xu, Pinghong,Browning, Nigel D.,Jentys, Andreas,Lercher, Johannes A.

, p. 3692 - 3704 (2015)

The distribution of metal cations and the morphology of unsupported NiMo, NiW, and NiMoW sulfide catalysts were explored qualitatively and quantitatively. In the bi- and trimetallic catalysts, Mo(W)S2 nanoparticles are deposited on Ni sulfide particles of varying stoichiometry and sizes (crystalline Ni9S8, and Ni3S4 were identified). These nanoparticles are stacks of Mo(W)S2 slabs with varying size, degrees of bending and mismatch between the slabs. High resolution electron microscopy and X-ray absorption spectroscopy based on particle modeling revealed a statistical distribution of Mo and W within individual layers in sulfide NiMoW, forming intralayer mixed Mo1-xWxS2. Ni is associated with MoS2, WS2, and Mo1-xWxS2 creating Ni-promoted phases. The incorporation of Ni at the edges of the slabs was the highest for sulfide NiMoW. This high concentration of Ni in sulfide NiMoW, as well as its long bent Mo1-xWxS2 slabs, were paralleled by the highest activity for nitrogen and sulfur removal from model hydrocarbons such as o-propylaniline and dibenzothiophene.

Transfer hydrogenation of alkenes using Ni/Ru/Pt/Au heteroquatermetallic nanoparticle catalysts: Sequential cooperation of multiple nano-metal species

Ito, Yoshikazu,Ohta, Hidetoshi,Yamada, Yoichi M. A.,Enoki, Toshiaki,Uozumi, Yasuhiro

, p. 12123 - 12126 (2014)

Quatermetallic alloy nanoparticles of Ni/Ru/Pt/Au were prepared and found to promote the catalytic transfer hydrogenation of non-activated alkenes bearing conjugating units (e.g., 4-phenyl-1-butene) with 2-propanol, where the composition metals, Ni, Ru, Pt, and Au, act cooperatively to provide significant catalytic ability. This journal is

Pd nanoparticles confined in mesoporous N-doped carbon silica supports: A synergistic effect between catalyst and support

Kerstien, Julius,Oliveira, Rafael L.,Schom?cker, Reinhard,Thomas, Arne

, p. 1385 - 1394 (2020)

Palladium nanoparticles of similar size were deposited on different supports, layers of carbon materials (with and without nitrogen doping) on the surface of a MCF (mesocellular foam) silica. For the generation of the N-doped carbon coatings, three different N sources were used to also investigate a possible influence of the N-doped carbon precursor and thus the structure of the N-doped carbons on their performance as catalyst support. These catalysts were tested for the Suzuki coupling and hydrogenation reactions. For the Suzuki reaction, the carbon coatings showed to increase dramatically the stability of the MCF material. Furthermore, when N-doped carbon coatings were applied, strong improvement of the stability of the catalysts was observed due to an enhanced interaction between metal nanoparticles and the support, preventing metal particle growth. In hydrogenation reactions, the presence of the N-doped carbon coating on the silica support increases the adsorption of aromatic compounds causing an enhancement of the catalytic activity of Pd NPs when compared to the non-doped supports.

Convenient preparation of metals deposited on solid supports and their use in organic synthesis

Majkosza, Mieczyslaw,Nieczypor, Piotr,Grela, Karol

, p. 10827 - 10836 (1998)

'High-surface alkali metals' can be conveniently prepared via deposition of corresponding metals on various supports such as sodium chloride, polyethylene, polypropylene and cross-linked polystyrene from their solutions in liquid ammonia. Alkali metals deposited on polymeric supports can be stored in form of stable suspensions in inert solvents and used for the acyloin and Dieckmann condensations and for preparation of organolithiums. Addition of the suspension of supported alkali metal to a solution of zinc chloride gave an active zinc on polymeric support, which can be used for the Reformatski and Barbier reactions.

Reaction Calorimetry in Microreactor Environments - Measuring Heat of Reaction by Isothermal Heat Flux Calorimetry

Glotz, Gabriel,Knoechel, Donald J.,Podmore, Philip,Gruber-Woelfler, Heidrun,Kappe, C. Oliver

, p. 763 - 770 (2017)

A novel setup to analyze the heat of reaction of different single- and multiphase reactions carried out in continuous flow is presented. The measurement principle of the calorimetric system is based on true heat flow measurements and therefore ensures precise calorimetric data within 10 mW resolution. In addition to the investigation of simple mixing phenomena (ethylene glycol and water), a number of exothermic, industrially relevant chemical transformations including the nitration of phenol, the reduction of nitrobenzene, as well as several oxidation and reduction processes, were investigated as model systems. For these experiments a commercially available batch calorimeter (ChemiSens CPA202) was equipped with a glass static mixer (250 μL) optionally connected to a tubular microreactor (PFA coil) allowing overall reaction volumes of up to ca. 5.5 mL. Experiments were performed by feeding individual streams with syringe pumps (alternatively substituting one liquid feed with a gaseous feed controlled by a mass flow controller) and mixing the feeds inside the glass static mixer contained in the thermostatted reactor zone of the calorimeter. By adjusting the residence time, volume, and flow rates, chemical transformations were driven to full conversion in order to obtain meaningful calorimetric data. A comparison with literature data indicates that the calorimetric flow system described herein provides comparable data to those obtained by standard batch calorimetry.

Chromow et al.

, p. 1360,1361; engl. Ausg. S. 1343, 1344 (1954)

Novel reaction of the low valent cobalt reagent generated using CoCl2 and NaBH4/C2H5OH in the presence of carbon monoxide

Satyanarayana, Nistala,Periasamy, Mariappan

, p. C33 - C36 (1987)

Low valent co balt species, prepared in situ in tetrahydrofuran (THF) by the reduction of CoCl2 with NaBH4/C2H5OH under carbon monoxide, isomerize of alkenes, reduce alkenes, and carbonylate benzyl halides under appropriate conditions.

Nickel boosts ring-opening activity of iridium

Ziaei-Azad, Hessam,Semagina, Natalia

, p. 885 - 894 (2014)

A variety of bimetallic Ni-Ir catalysts were synthesised by preforming nanoparticles in the presence of polyvinylpyrrolidone, followed by deposition on γ-alumina and high-temperature polymer removal. The Ni-Ir (1:1 molar ratio) nanoparticles prepared by the hydrogen-sacrificial technique (Ir reduction on the preformed Ni nanoparticles with surface Ni hydride) allowed increasing indane ring opening activity per total amount of Ir as compared to monometallic Ir. The simultaneous reduction of Ni and Ir precursors was not as efficient. The catalysts were characterised with UV/Vis spectroscopy, TEM, temperature-programmed reduction, CO2 temperature-programmed desorption, CO diffuse reflectance Fourier transform spectroscopy, X-ray photoelectron spectroscopy and CHN analysis. The study only explored the catalyst's metal function and allows saving rare and expensive iridium without loss of its outstanding performance as a ring-opening catalyst. Save the rare: To avoid inefficient use of rare and expensive catalytic metals, iridium atoms are placed only in the outermost layer of the nanoparticles, with inexpensive metal (nickel) inside, which boosts the catalytic performance.

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Soffer,Soffer,Sherk

, p. 1435,1436 (1945)

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Ionic liquid-initiated polymerization of epoxides: A useful strategy for the preparation of Pd-doped polyether catalysts

Arnold, Ulrich,Altesleben, Christiane,Behrens, Silke,Essig, Sarah,Lautenschütz, Ludger,Schild, Dieter,Sauer, J?rg

, p. 116 - 124 (2015)

Palladium compounds (Pd(OAc)2 and Pd(acac)2) were dissolved in commercially available epoxy resins (glycidyl derivatives of bisphenol A and p-aminophenol) and the formulations were polymerized employing the ionic liquid 1-ethyl-2-methylimidazolium acetate (EMIM acetate) as polymerization initiator. Thus, palladium species could be incorporated in the network of the resulting polyether materials. Polymerization reactions were investigated by DSC and the curing behavior of different formulations was compared. High polymerization enthalpies were observed indicating high crosslinking in the materials. Accordingly, the materials exhibited high glass transition temperatures and thermogravimetric data revealed high thermal stability. Due to the good solubility of the palladium compounds in the epoxy resins, a widely homogeneous dispersion of palladium species in the polyether matrix could be realized. This was confirmed by SEM-EDX and TEM measurements. XPS measurements revealed that reduction of Pd(II) to Pd(0) species occurred during catalyst preparation and this was also proven by XRD. The materials were ground and successfully employed as catalysts for the hydrogenation of several alkenes under mild reaction conditions. High conversions and selectivities could be reached within a few hours at room temperature and moderate hydrogen pressure of 2.5 bar. Palladium leaching from the catalysts to reaction solutions was investigated. To determine very low quantities, metal concentrations were enriched by removal of volatile components. Subsequent ICP-AES measurements revealed low palladium contents in the range of a few μg. These amounts correspond to values around 0.007% with respect to palladium originally loaded on the polymer. Catalyst recycling experiments were also carried out and it was shown that the catalysts can be employed in numerous consecutive reactions without any catalyst treatment and without loss of activity. Within a series of reactions, palladium leaching decreased while catalytic activity was not affected.

Activation of Reducing Agents. Sodium Hydride Containing Complex Reducing Agents. 33. NiCRA's and NiCRAL's as New Efficient Desulfurizing Reagents

Becker, Sandrine,Fort, Yves,Vanderesse, Regis,Caubere. Paul

, p. 4848 - 4853 (1989)

It is shown that nickel-containing complex reducing agents alone or in the presence of 2,2'-bipyridine (NiCRA and NiCRAL-bpy, respectively) are very efficient in the desulfurization of sulfur containing organic compounds.A number of functional groups are resistant.Advantages of the inexpensive and nonpyrophoric CRA's are their easy preparation and handling.The mechanism of these desulfuryzations are discussed and compared to those with Ni(0) complexes.

Coupling of titanacyclopentadienes with a cp ligand and elimination of one substituent

Mizukami, Yuki,Li, Haijun,Nakajima, Kiyohiko,Song, Zhiyi,Takahashi, Tamotsu

, p. 8899 - 8903 (2014)

Titanacyclopentadienes, prepared from [Cp2TiBu2] and either two equivalents of an alkyne or a diyne, were treated with PMe 3 (3 equiv) at 50C for 3 h and then with azobenzene at room temperature for 12 h to give 4,5,6-trisubstituted indene derivatives with the loss of one substituent in good yields. This reaction contrasts sharply with our previously reported reaction for the formation of 4,5,6,7-tetrasubstituted indene derivatives without the loss of substituents by the treatment of titanacyclopentadienes with azobenzene without PMe3. 13C NMR spectroscopy of the product derived from a 13C-enriched complex revealed that the five carbon atoms originating from a Cp ligand were arranged linearly in the trisubstituted indene derivatives, in contrast to the 4,5,6,7-tetrasubsituted indene derivatives, in which the corresponding five carbon atoms are arranged in a ring.

Continuous flow reduction of artemisinic acid utilizing multi-injection strategies - Closing the gap towards a fully continuous synthesis of antimalarial drugs

Pieber, Bartholom?us,Glasnov, Toma,Kappe, C. Oliver

, p. 4368 - 4376 (2015)

One of the rare alternative reagents for the reduction of carbon-carbon double bonds is diimide (HN=NH), which can be generated in situ from hydrazine hydrate (N2H4·H2O) and O2. Although this selective method is extremely clean and powerful, it is rarely used, as the rate-determining oxidation of hydrazine in the absence of a catalyst is relatively slow using conventional batch protocols. A continuous high-temperature/high-pressure methodology dramatically enhances the initial oxidation step, at the same time allowing for a safe and scalable processing of the hazardous reaction mixture. Simple alkenes can be selectively reduced within 10-20 min at 100-120°C and 20 bar O2 pressure. The development of a multi-injection reactor platform for the periodic addition of N2H4·H2O enables the reduction of less reactive olefins even at lower reaction temperatures. This concept was utilized for the highly selective reduction of artemisinic acid to dihydroartemisinic acid, the precursor molecule for the semisynthesis of the antimalarial drug artemisinin. The industrially relevant reduction was achieved by using four consecutive liquid feeds (of N2H4·H2O) and residence time units resulting in a highly selective reduction within approximately 40 min at 60°C and 20 bar O2 pressure, providing dihydroartemisinic acid in ≥93% yield and ≥95% selectivity.

Effective hydrodeoxygenation of lignin-derived phenols using bimetallic RuRe catalysts: Effect of carbon supports

Jung, Kyung Bin,Lee, Jinho,Ha, Jeong-Myeong,Lee, Hyunjoo,Suh, Dong Jin,Jun, Chul-Ho,Jae, Jungho

, p. 191 - 199 (2018)

We have previously shown that an activated carbon-supported ruthenium catalyst promoted with ReOx (RuRe/AC) is highly active for the hydrodeoxygenation (HDO) of lignin-derived phenols (e.g., guaiacol). In this work, we have investigated the effect of carbon supports on the structure and HDO activity of bimetallic RuRe particles using three different carbon supports, i.e., activated carbon (AC), carbon black (Vulcan carbon, VC), multi-walled carbon nanotube (MWCNT). The MWCNT- and VC-supported catalysts show remarkably enhanced activity and hydrocarbon selectivity for the HDO of a range of phenolic molecules (i.e., guaiacol, eugenol, benzyl phenyl ether) compared to RuRe/AC. STEM-EDS and XPS analyses reveal that bimetallic RuRe particles are more common than monometallic Ru or Re particles in the VC- and MWCNT-supported catalysts, and hexavalent rhenium species are more easily reduced to tetravalent rhenium during the HDO reactions in these catalysts, suggesting that Ru and Re in close proximity are required for the efficient hydrogenolysis of phenols. The formation of bimetallic particles on the AC surface is likely hindered by high microporosity and high surface oxygen functionalities, both of which restrict the mobility of Re and Ru for assembly.

COMPARATIVE INVESTIGATION OF THE CATALYTIC PROPERTIES OF CRYSTALLINE ALUMOSILICATES OF VARIOUS TYPES. COMMUNICATION 3. SELECTIVITY OF THE CONVERSION OF METHANOL ON ZEOLITES OF VARIOUS TYPES

Stepanov, V. G.,Gonyshev, A. P.,Ione, K. G.

, p. 1567 - 1572 (1982)

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CATALYTIC PROPERTIES OF GROUP VIII METAL COMPOUNDS SUPPORTED ON A POLYMERIC CARREIR. 3. NICKEL AND COBALT COMPLEXES SUPPORTED ON CARRIERS CONTAINING COORDINATION GROUPS BASED ON PHOSPHORUS IN THE HYDROGENATION AND ISOMERIZATION REACTIONS OF ALLYLBENZENE

Sukhobok, L. N.,Potapov, G. P.,Polkovnikov, B. D.,Luksha, V. G.,Krutii, V. N.

, p. 763 - 764 (1983)

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Hydrocarbon-soluble nanocatalysts with no bulk phase: Coplanar, two-coordinate arrays of the base metals

Camacho-Bunquin, Jeffrey,Ferguson, Michael J.,Stryker, Jeffrey M.

, p. 5537 - 5540 (2013)

A structurally unique class of hydrocarbon-soluble, ancillary-ligand-free, tetrametallic Co(I) and Ni(I) clusters is reported. The highly unsaturated complexes are supported by simple, sterically bulky phosphoranimide ligands, one per metal. The electron-rich nitrogen centers are strongly bridging but sterically limited to bimetallic interactions. The hydrocarbon-soluble clusters consist of four coplanar metal centers, mutually bridged by single nitrogen atoms. Each metal center is monovalent, rigorously linear, and two-coordinate. The clusters are in essence two-dimensional atomic-scale "molecular squares," a structural motif adapted from supramolecular chemistry. Both clusters exhibit high solution-phase magnetic susceptibility at room temperature, suggesting the potential for applications in molecular electronics. Designed to be catalyst precursors, both clusters exhibit high activity for catalytic hydrogenation of unsaturated hydrocarbons at low pressure and temperature.

An unprecedented iron-catalyzed cross-coupling of primary and secondary alkyl Grignard reagents with non-activated aryl chlorides

Perry, Marc C.,Gillett, Amber N.,Law, Tyler C.

, p. 4436 - 4439 (2012)

The use of N-heterocyclic carbene ligands in the iron-catalyzed cross-coupling of alkyl Grignards has allowed, for the first time, coupling of non-activated, electron rich aryl chlorides. Surprisingly, the tetrahydrate of FeCl2 was found to be a better pre-catalyst than anhydrous FeCl 2. Primary Grignard reagents coupled in excellent yields while secondary Grignard reagents coupled in modest yields. The use of acyclic secondary Grignard reagents resulted in the formation of isomers in addition to the desired product. These isomeric products were formed via reversible β-hydrogen elimination, indicating that the cross-coupling proceeds through an ionic pathway.

STRUCTURE AND CATALYTIC ACTIVITY OF SUPPORTED METAL COMPLEXES: COMMUNICATION 2. SYNTHESIS OF RHODIUM COMPLEXES ON SILICA GEL MODIFIED BY PHOSPHORUS- AND NIROGEN-CONTAINING LIGANDS

Dovganyuk, V. F.,Lafer, L. I.,Isaeva, V. I.,Dykh, Zh. L.,Yakerson, V. I.,Sharf, V. Z.

, p. 2465 - 2470 (1987)

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Irwin,McQuillin

, p. 1937 (1968)

Heterolysis of Dihydrogen by Nucleophilic Calcium Alkyls

Wilson, Andrew S. S.,Dinoi, Chiara,Hill, Michael S.,Mahon, Mary F.,Maron, Laurent

, p. 15500 - 15504 (2018)

β-Diketiminato (BDI) calcium alkyl derivatives undergo hydrogenolysis with H2 to regenerate [(BDI)CaH]2, allowing the catalytic hydrogenation of a wide range of 1-alkenes and norbornene under very mild conditions (2 bar H2, 298 K). The reactions are deduced to take place with the retention of the dimeric structures of the calcium hydrido-alkyl and alkyl intermediates via a well-defined sequence of Ca?H/C=C insertion and Ca?C hydrogenation events. This latter deduction is strongly supported by DFT calculations (B3PW91) performed on the 1-hexene/H2 system, which also indicates that the hydrogenation transition states display features which discriminate them from a classical σ-bond metathesis mechanism. In particular, NBO analysis identifies a strong second order interaction between the filled α-methylene sp3 orbital of the n-hexyl chain and the σ* orbital of the H2 molecule, signifying that the H?H bond is broken by what is effectively the nucleophilic displacement of hydride by the organic substituent.

Size- and structure-controlled mono- and bimetallic Ir-Pd nanoparticles in selective ring opening of indan

Ziaei-Azad, Hessam,Yin, Cindy-Xing,Shen, Jing,Hu, Yongfeng,Karpuzov, Dimitre,Semagina, Natalia

, p. 113 - 124 (2013)

Nearly monodispersed 1.6 nm Ir, 2.3 nm Pd nanoparticles, 2.7 nm Pd(core)-Ir(shell) and 2.2 nm Pd-Ir alloys with mixed surface atoms were synthesised in the presence of polyvinylpyrrolidone (PVP) and studied in the atmospheric ring opening of indan. The na

One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride

Epifanov, Maxim,Mo, Jia Yi,Dubois, Rudy,Yu, Hao,Sammis, Glenn M.

, p. 3768 - 3777 (2021/03/01)

Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.

Room temperature iron catalyzed transfer hydrogenation usingn-butanol and poly(methylhydrosiloxane)

Coles, Nathan T.,Linford-Wood, Thomas G.,Webster, Ruth L.

supporting information, p. 2703 - 2709 (2021/04/21)

Reduction of carbon-carbon double bonds is reported using a three-coordinate iron(ii) β-diketiminate pre-catalyst. The reaction is believed to proceedviaa formal transfer hydrogenation using poly(methylhydrosiloxane), PMHS, as the hydride donor and a bio-alcohol as the proton source. The reaction proceeds well usingn-butanol and ethanol, withn-butanol being used for substrate scoping studies. Allyl arene substrates, styrenes and aliphatic substrates all undergo reduction at room temperature. Unfortunately, clean transfer of a deuterium atom usingd-alcohol does not take place, indicating a complex catalytic mechanism. However, changing the deuterium source tod-aniline gives close to complete regioselectivity for mono-deuteration of the terminal position of the double bond. Finally, we demonstrate that efficient dehydrocoupling of alcohol and PMHS can be undertaken using the same pre-catalyst, giving high yields of H2within 30 minutes at room temperature.

Photoredox-Catalyzed Simultaneous Olefin Hydrogenation and Alcohol Oxidation over Crystalline Porous Polymeric Carbon Nitride

Qiu, Chuntian,Sun, Yangyang,Xu, Yangsen,Zhang, Bing,Zhang, Xu,Yu, Lei,Su, Chenliang

, p. 3344 - 3350 (2021/07/26)

Booming of photocatalytic water splitting technology (PWST) opens a new avenue for the sustainable synthesis of high-value-added hydrogenated and oxidized fine chemicals, in which the design of efficient semiconductors for the in-situ and synergistic utilization of photogenerated redox centers are key roles. Herein, a porous polymeric carbon nitride (PPCN) with a crystalline backbone was constructed for visible light-induced photocatalytic hydrogen generation by photoexcited electrons, followed by in-situ utilization for olefin hydrogenation. Simultaneously, various alcohols were selectively transformed to valuable aldehydes or ketones by photoexcited holes. The porosity of PPCN provided it with a large surface area and a short transfer path for photogenerated carriers from the bulk to the surface, and the crystalline structure facilitated photogenerated charge transfer and separation, thus enhancing the overall photocatalytic performance. High reactivity and selectivity, good functionality tolerance, and broad reaction scope were achieved by this concerted photocatalysis system. The results contribute to the development of highly efficient semiconductor photocatalysts and synergistic redox reaction systems based on PWST for high-value-added fine chemical production.

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