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3558-60-9

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3558-60-9 Usage

Description

Methyl phenethyl ether has a powerful diffusive and penetrating odor with a warm, floral note. It is "grassy" and pungent on dilution. May be prepared by catalytic reduction of phenylacetaldehyde dimethyl acetal; from phenylethyl alcohol and methanol.

Chemical Properties

Different sources of media describe the Chemical Properties of 3558-60-9 differently. You can refer to the following data:
1. Methyl phenethyl ether has a powerful, diffusive and penetrating odor with a warm, floral note; “grassy” and pungent on dilution.
2. (2-Methoxyethyl)benzene is a colorless liquid with a sharp, rosy-green odor. It is used in oriental-type perfumes as well as in artificial keora oil.

Occurrence

Reported as occurring in Pandanus odoratissimus and in the oil of Tagetes signata and Scotch spearmint oil; also in litchi

Uses

Phenylethyl methyl ether is a volatile compound that can be found in Litchi wine (and Litchi fruit) during winemaking. Phenylethyl methyl ether is also an additive to perfumes, detergents and soaps.

Preparation

By catalytic reduction of phenylacetaldehyde dimethyl acetal; from phenylethyl alcohol and methanol

Flammability and Explosibility

Nonflammable

Check Digit Verification of cas no

The CAS Registry Mumber 3558-60-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,5 and 8 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 3558-60:
(6*3)+(5*5)+(4*5)+(3*8)+(2*6)+(1*0)=99
99 % 10 = 9
So 3558-60-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O/c1-10-8-7-9-5-3-2-4-6-9/h2-6H,7-8H2,1H3

3558-60-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (2-Methoxyethyl)benzene

1.2 Other means of identification

Product number -
Other names 2-Methoxyethylbenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:3558-60-9 SDS

3558-60-9Synthetic route

iodobenzene
591-50-4

iodobenzene

2-Bromoethyl methyl ether
6482-24-2

2-Bromoethyl methyl ether

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With triethanolamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; [Ni(2,2′:6′,2''-terpyridine)(pyridine)(CH3CN)2](PF6)2 In acetonitrile at 23 - 28℃; for 12h; Inert atmosphere; Sealed tube; Irradiation;96%
methanol
67-56-1

methanol

(2-phenyl-ethyl) phenyl selenide
65275-36-7

(2-phenyl-ethyl) phenyl selenide

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid at 25℃; for 1h;95%
2-phenylethanol
60-12-8

2-phenylethanol

methyl trimethylamine phosphate
77891-02-2

methyl trimethylamine phosphate

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With potassium chloride; sodium sulfite at 85℃; for 4h; Temperature;95%
methanol
67-56-1

methanol

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With silver tetrafluoroborate; 1-(2-bromo-1,1-dimethoxyethyl)benzene at 25℃; for 4h;90%
(i) HgO, aq. HClO4, (ii) /BRN= 507487/; Multistep reaction;
With tetrafluoroboric acid; HgBF4
at 138 - 145℃; under 8250.7 Torr; for 1.8h; Irradiation;38 % Turnov.
at 140℃; under 7500.6 Torr; for 2h; Irradiation; Yield given;
2-phenylethanol
60-12-8

2-phenylethanol

methyl iodide
74-88-4

methyl iodide

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
Stage #1: 2-phenylethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 72h;
86%
With aluminum oxide; potassium fluoride In acetonitrile for 43h;66%
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h;65%
1-(2-methoxyvinyl)benzene
4747-15-3

1-(2-methoxyvinyl)benzene

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With ammonia; calcium In tetrahydrofuran at -33℃; for 2h;85%
benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With (PPh3)(CO)4MnC(O)CH3; phenylsilane In benzene-d6 for 2h;83%
With triethylsilane; trimethylsilyl trifluoromethanesulfonate; titanium tetrachloride In dichloromethane at 20℃; for 20h;40%
2-phenylethanol
60-12-8

2-phenylethanol

dimethyl sulfate
77-78-1

dimethyl sulfate

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With sodium hydroxide; zirconium (benzyldiethylammoniomethylphosphonate chloride) phosphate In ethanol; water; Petroleum ether at 42℃; for 8h;81.3%
With sodium hydride In diethyl ether for 20h; Heating;60%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide
2-phenylethanol
60-12-8

2-phenylethanol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

A

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

B

methyl (2-phenyl)ethyl carbonate
1796-66-3

methyl (2-phenyl)ethyl carbonate

Conditions
ConditionsYield
With Amberlyst 15 for 12h; Reflux;A 14%
B 79%
methanol
67-56-1

methanol

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

A

styrene
100-42-5

styrene

B

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
In methanol at 95℃; under 5475.4 Torr; for 0.0283333h; Irradiation;A 75%
B 9%
1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

A

styrene
100-42-5

styrene

B

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With sodium methylate In methanol at 95℃; under 5475.4 Torr; for 0.0283333h; Irradiation;A 75%
B 9%
methanol
67-56-1

methanol

ethene
74-85-1

ethene

trimethylphenylsilane
768-32-1

trimethylphenylsilane

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With (triphenylphosphine)gold(I) chloride; 1-(trifluoromethanesulfonyloxy)-1,2-benziodoxol-3(1H)-one In acetonitrile at 50℃; under 750.075 Torr; for 18h; Reagent/catalyst; Temperature; Solvent; Sealed tube;72%
methanol
67-56-1

methanol

2-phenylethyl phenyl telluride
81609-30-5

2-phenylethyl phenyl telluride

A

styrene
100-42-5

styrene

B

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid at 20 - 25℃; for 1h;A 14%
B 67%
With 3-chloro-benzenecarboperoxoic acid at 20 - 25℃; for 1h;A 14 % Chromat.
B 67%
phenylacetaldehyde
122-78-1

phenylacetaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; toluene-4-sulfonic acid In methanol at 130℃; under 22502.3 Torr; for 6h; Autoclave; Inert atmosphere;66.5%
sodium phenethylate
22096-25-9

sodium phenethylate

methyl iodide
74-88-4

methyl iodide

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
In dimethyl sulfoxide63%
styrene
100-42-5

styrene

methanol
67-56-1

methanol

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With terephthalonitrile In acetonitrile for 2h; UV-irradiation;35%
With N,N′-bis(2-ethylhexyl)-1,7-dicyanoperylene-3,4:9,10-bis(dicarboximide); thiophenol In dichloromethane at 30℃; for 42h; Irradiation; Inert atmosphere; regioselective reaction;32%
Dimethoxymethane
109-87-5

Dimethoxymethane

benzylmagnesium chloride

benzylmagnesium chloride

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
at 150℃;
bromethyl methyl ether
13057-17-5

bromethyl methyl ether

benzylmagnesium chloride

benzylmagnesium chloride

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

2-phenylethanol
60-12-8

2-phenylethanol

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With sodium hydroxide; dimethyl sulfate
With diazomethane; diethyl ether; boron trifluoride diethyl etherate
diethyl ether
60-29-7

diethyl ether

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

benzylmagnesium chloride

benzylmagnesium chloride

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

benzylmagnesium chloride
6921-34-2

benzylmagnesium chloride

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With diethyl ether
2-chloroethyl methyl ether
627-42-9

2-chloroethyl methyl ether

phenyllithium
591-51-5

phenyllithium

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With diethyl ether
diethyl ether
60-29-7

diethyl ether

phenyllithium
591-51-5

phenyllithium

2-Bromoethyl methyl ether
6482-24-2

2-Bromoethyl methyl ether

A

bromobenzene
108-86-1

bromobenzene

B

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

C

benzene
71-43-2

benzene

phenyllithium
591-51-5

phenyllithium

2-Bromoethyl methyl ether
6482-24-2

2-Bromoethyl methyl ether

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With diethyl ether
bromethyl methyl ether
13057-17-5

bromethyl methyl ether

benzylmagnesium chloride
6921-34-2

benzylmagnesium chloride

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

phenylacetaldehyde dimethyl acetal
101-48-4

phenylacetaldehyde dimethyl acetal

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

Conditions
ConditionsYield
With hydrogen; nickel at 180℃;
With carbon monoxide; hydrogen; dicobalt octacarbonyl at 180℃; under 124116 Torr;
styrene
100-42-5

styrene

methanol
67-56-1

methanol

A

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

B

1,4-diphenylbutane
1083-56-3

1,4-diphenylbutane

C

3-phenyl-2-oxabutane
4013-34-7

3-phenyl-2-oxabutane

D

1,2-dimethoxyethylbenzene
32345-80-5, 4013-37-0

1,2-dimethoxyethylbenzene

Conditions
ConditionsYield
With potassium hydroxide; borane-THF 1) THF, 2) THF, Pt-anode, 30 mF; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
methanol
67-56-1

methanol

2-phenylethanol
60-12-8

2-phenylethanol

A

styrene
100-42-5

styrene

B

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

C

3-phenyl-2-oxabutane
4013-34-7

3-phenyl-2-oxabutane

D

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With methane; oxygen at 37.5℃; Product distribution; Irradiation; different partial pressures of components;
methanol
67-56-1

methanol

1-fluoro-2-phenylethane
458-87-7

1-fluoro-2-phenylethane

A

styrene
100-42-5

styrene

B

benzyl methyl ether
538-86-3

benzyl methyl ether

C

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

D

3-phenyl-2-oxabutane
4013-34-7

3-phenyl-2-oxabutane

E

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With methane; oxygen at 37.5℃; Product distribution; Irradiation; different bulk gas and methanol partial pressures;
2-phenylethanol
60-12-8

2-phenylethanol

A

styrene
100-42-5

styrene

B

biphenyl
92-52-4

biphenyl

C

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

D

ethylbenzene
100-41-4

ethylbenzene

E

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

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

F

toluene
108-88-3

toluene

Conditions
ConditionsYield
at 446.4 - 493.7℃; Product distribution; Kinetics; thermal elimination;
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

methyl 2-phenyl(2,2-(2)H)ethyl ether

methyl 2-phenyl(2,2-(2)H)ethyl ether

Conditions
ConditionsYield
With hydrogen; water-d2; palladium on activated charcoal at 20℃; for 72h;88%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

(1‐bromo‐2‐methoxyethyl)benzene
29610-84-2

(1‐bromo‐2‐methoxyethyl)benzene

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h; Heating / reflux;84%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

acetophenone
98-86-2

acetophenone

2-(4-(2-methoxyethyl)phenyl)-1-phenylethan-1-one

2-(4-(2-methoxyethyl)phenyl)-1-phenylethan-1-one

Conditions
ConditionsYield
Stage #1: 1-methoxy-2-phenylethane With thianthrene-5-oxide; trifluoromethylsulfonic anhydride In acetonitrile at -20 - 20℃; for 0.666667h; Inert atmosphere; Schlenk technique;
Stage #2: acetophenone With palladium diacetate; cesium fluoride; XPhos In N,N-dimethyl-formamide; acetonitrile at 80℃; for 11h; Inert atmosphere; Schlenk technique;
80%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

C9H8(2)H4O

C9H8(2)H4O

Conditions
ConditionsYield
With hydrogen; water-d2; palladium on activated charcoal at 110℃; under 760.051 Torr; for 24h;79%
pyrrole
109-97-7

pyrrole

1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

1-phenethyl-1H-pyrrole
50691-29-7

1-phenethyl-1H-pyrrole

Conditions
ConditionsYield
With phosphazene base-P4-tert-butyl In 1,4-dioxane; hexane at 130℃; for 24h; Sealed tube; Inert atmosphere; Molecular sieve;79%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

A

2-phenylethyl chloride
622-24-2

2-phenylethyl chloride

B

acetic acid phenethyl ester
103-45-7

acetic acid phenethyl ester

Conditions
ConditionsYield
With acetyl chloride; zinc In Petroleum ether at 28℃; for 4h;A 78%
B 20%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

acetyl chloride
75-36-5

acetyl chloride

A

2-phenylethyl chloride
622-24-2

2-phenylethyl chloride

B

acetic acid phenethyl ester
103-45-7

acetic acid phenethyl ester

Conditions
ConditionsYield
With zinc In Petroleum ether at 28℃; for 4h;A 78%
B 20%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

phenylpropyolic acid
637-44-5

phenylpropyolic acid

2-(1-methoxy-2-phenylethyl)-4-phenyl-2H-1,2,3-triazole

2-(1-methoxy-2-phenylethyl)-4-phenyl-2H-1,2,3-triazole

Conditions
ConditionsYield
With tert.-butylhydroperoxide; trimethylsilylazide; copper dichloride at 80℃; for 12h;68%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

ethylbenzene
100-41-4

ethylbenzene

Conditions
ConditionsYield
With hydrogen; AIOTfbpy-Pd In 1,2-dichloro-ethane at 130℃; under 750.075 Torr; for 24h; Glovebox; Inert atmosphere;61%
With hydrogen; Al(OH)(2,2'-bipyridine-5,5'-dicarboxylic acid)0.81(PdCl2)0.48(OTf)0.38 In 1,2-dichloro-ethane at 130℃; under 750.075 Torr; for 24h;55%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

ethyl acrylate
140-88-5

ethyl acrylate

A

(2E,2'E)-diethyl 3,3'-(2-(2-methoxyethyl)-1,3-phenylene)diacrylate
1450816-66-6

(2E,2'E)-diethyl 3,3'-(2-(2-methoxyethyl)-1,3-phenylene)diacrylate

B

(E)-ethyl 3-(2-(2-methoxyethyl)phenyl)acrylate
1450816-65-5

(E)-ethyl 3-(2-(2-methoxyethyl)phenyl)acrylate

Conditions
ConditionsYield
With silver (II) carbonate; palladium diacetate; N-acetylglycine at 80℃; for 48h; Sealed tube;A 25%
B 60%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

aniline
62-53-3

aniline

A

2-benzyl-2,3-dihydrobenzo[d]thiazole
31230-89-4

2-benzyl-2,3-dihydrobenzo[d]thiazole

B

2-benzylbenzothiazole
6265-94-7

2-benzylbenzothiazole

Conditions
ConditionsYield
With tert.-butylhydroperoxide; sulfur; potassium iodide In water; dimethyl sulfoxide at 130℃; for 6h;A 15%
B 52%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

phenylacetylene
536-74-3

phenylacetylene

2-(1-methoxy-2-phenylethyl)-4-phenyl-2H-1,2,3-triazole

2-(1-methoxy-2-phenylethyl)-4-phenyl-2H-1,2,3-triazole

Conditions
ConditionsYield
With tert.-butylhydroperoxide; trimethylsilylazide; copper(l) chloride at 80℃; for 16h; Sealed tube; regioselective reaction;51%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

phenyl(hydroxy)(tetrafluoroborato)-λ3-iodane 18-crown-6 complex (1:1)

phenyl(hydroxy)(tetrafluoroborato)-λ3-iodane 18-crown-6 complex (1:1)

A

[2-(2-methoxyethyl)phenyl](phenyl)(tetrafluoroborato)-λ(3)-iodane

[2-(2-methoxyethyl)phenyl](phenyl)(tetrafluoroborato)-λ(3)-iodane

B

[4-(2-methoxyethyl)phenyl](phenyl)(tetrafluooroborato)-λ(3)-iodane

[4-(2-methoxyethyl)phenyl](phenyl)(tetrafluooroborato)-λ(3)-iodane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water In dichloromethane at 45℃; for 6h; Inert atmosphere;A 23%
B 39%
1-methoxy-2-phenylethane
3558-60-9

1-methoxy-2-phenylethane

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

A

4-methyl-N-(2-phenylethyl)benzenesulfonamide
5450-75-9

4-methyl-N-(2-phenylethyl)benzenesulfonamide

B

N-methyl-p-toluenesulfonylamide
640-61-9

N-methyl-p-toluenesulfonylamide

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In toluene at 170℃; for 25h;A 38%
B 19%

3558-60-9Relevant articles and documents

Intramolecular interactions in ortho-methoxyalkylphenylboronic acids and their catechol esters

Adamczyk-Wozniak, Agnieszka,Borys, Krzysztof M.,Czerwinska, Karolina,Gierczyk, Blazej,Jakubczyk, Michal,Madura, Izabela D.,Sporzynski, Andrzej,Tomecka, Ewelina

, p. 616 - 621 (2013)

(Graph Presented) Catechol esters of ortho-methoxyalkylphenylboronic acids have been synthesized and characterized by 17O NMR spectroscopy. The results were compared with the data for the parent acids. The influence of intramolecular and intermolecular hydrogen bonds on the properties of the boronic acids has been discussed. The 17O NMR data for the boronic esters proved that there are no O → B interactions in the investigated compounds. This fact is connected with weak Lewis acidity of the parent acids and their low sugars' receptors activity. Crystal structure of ortho -methoxyphenylboronic acid catechol ester was determined.

Photoredox-Assisted Reductive Cross-Coupling: Mechanistic Insight into Catalytic Aryl-Alkyl Cross-Couplings

Paul, Avishek,Smith, Mark D.,Vannucci, Aaron K.

, p. 1996 - 2003 (2017/02/26)

Here, we describe a photoredox-assisted catalytic system for the direct reductive coupling of two carbon electrophiles. Recent advances have shown that nickel catalysts are active toward the coupling of sp3-carbon electrophiles and that well-controlled, light-driven coupling systems are possible. Our system, composed of a nickel catalyst, an iridium photosensitizer, and an amine electron donor, is capable of coupling halocarbons with high yields. Spectroscopic studies support a mechanism where under visible light irradiation the Ir photosensitizer in conjunction with triethanolamine are capable of reducing a nickel catalyst and activating the catalyst toward cross-coupling of carbon electrophiles. The synthetic methodology developed here operates at low 1 mol % catalyst and photosensitizer loadings. The catalytic system also operates without reaction additives such as inorganic salts or bases. A general and effective sp2-sp3 cross-coupling scheme has been achieved that exhibits tolerance to a wide array of functional groups.

Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation

Weiser, Martin,Hermann, Sergej,Penner, Alexander,Wagenknecht, Hans-Achim

, p. 568 - 575 (2015/06/08)

The nucleophilic addition of methanol and other alcohols to 1,1-diphenylethylene (1) and styrene (6) into the Markovnikov- and anti-Markovnikov-type products was selectively achieved with 1-(N,N-dimethylamino)pyrene (Py) and 1,7-dicyanoperylene-3,4:9,10-tetracarboxylic acid bisimide (PDI) as photoredox catalysts. The regioselectivity was controlled by the photocatalyst. For the reductive mode towards the Markovnikov-type regioselectivity, Py was applied as photocatalyst and triethylamine as electron shuttle. This approach was also used for intramolecular additions. For the oxidative mode towards the anti-Markovnikov-type regioselectivety, PDI was applied together with Ph-SH as additive. Photocatalytic additions of a variety of alcohols gave the corresponding products in good to excellent yields. The proposed photocatalytic electron transfer mechanism was supported by detection of the PDI radical anion as key intermediate and by comparison of two intramolecular reactions with different electron density. Representative mesoflow reactor experiments allowed to significantly shorten the irradiation times and to use sunlight as "green"light source.

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