e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetraethylammonium Bromide??Catalyzed Oxidative Thioesterification of Aldehydes and Alcohols

X Zhu, Y Shi, H Mao, Y Cheng…

Index: Zhu, Xuebin; Shi, Yan; Mao, Haibin; Cheng, Yixiang; Zhu, Chengjian Advanced Synthesis and Catalysis, 2013 , vol. 355, # 18 p. 3558 - 3562

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Citation Number: 23

Abstract

Abstract: A metal-free, tetraethylammonium bromide-catalyzed oxidative coupling of aldehydes or alcohols with thiophenols or disulfides has been developed. This protocol affords an efficient and inexpensive approach to the synthesis of a wide range of thioesters in high yields. Keywords: metal-free conditions; oxidative coupling; tetraalkylammonium bromides; thioesterification

Thiophenol Structure

3-Chlorobenzaldehyde Structure

3-Chlorobenzaldehyde

~87%

S-phenyl 3-chlorobenzenecarbothioate Structure

S-phenyl 3-chlo...

Thiophenol Structure

4-Cyanobenzaldehyde Structure

4-Cyanobenzaldehyde

~70%

S-phenyl 4-cyanobenzenecarbothioate Structure

S-phenyl 4-cyan...

4-(Hydroxymethyl)benzonitrile Structure

4-(Hydroxymethy...

Thiophenol Structure

~65%

S-phenyl 4-cyanobenzenecarbothioate Structure

S-phenyl 4-cyan...

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

4-Chlorothiophenol Structure

4-Chlorothiophenol

~89%

Benzenecarbothioicacid, 4-chloro-, S-(4-chlorophenyl) ester Structure

Benzenecarbothi...

Benzaldehyde Structure

Thiophenol Structure

~88%

Benzoic acid, thio-, S-phenyl ester Structure

Benzoic acid, t...

Thiophenol Structure

Benzyl alcohol Structure

~89%

Benzoic acid, thio-, S-phenyl ester Structure

Benzoic acid, t...

2-Thiophenecarboxaldehyde Structure

2-Thiophenecarb...

Thiophenol Structure

~80%

Thiophene-2-carbothioic acid S-phenyl ester Structure

Thiophene-2-car...

Thiophen-2-ylmethanol Structure

Thiophen-2-ylme...

Thiophenol Structure

~77%

Thiophene-2-carbothioic acid S-phenyl ester Structure

Thiophene-2-car...

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

Diphenyl disulfide Structure

Diphenyl disulfide

~89%

S-Phenyl 4-chlorobenzenecarbothioate Structure

S-Phenyl 4-chlo...

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

Thiophenol Structure

~92%

S-Phenyl 4-chlorobenzenecarbothioate Structure

S-Phenyl 4-chlo...

Thiophenol Structure

p-chlorobenzylalcohol Structure

p-chlorobenzyla...

~90%

S-Phenyl 4-chlorobenzenecarbothioate Structure

S-Phenyl 4-chlo...

p-chlorobenzylalcohol Structure

p-chlorobenzyla...

Diphenyl disulfide Structure

Diphenyl disulfide

~89%

S-Phenyl 4-chlorobenzenecarbothioate Structure

S-Phenyl 4-chlo...

3-Phenylpropanal Structure

3-Phenylpropanal

Thiophenol Structure

~82%

S-phenyl 3-phenylpropanethioate Structure

S-phenyl 3-phen...

2-Chlorobenzyl alcohol Structure

2-Chlorobenzyl ...

Thiophenol Structure

~91%

S-phenyl 2-chlorobenzenecarbothioate Structure

S-phenyl 2-chlo...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

Thiophenol Structure

~88%

S-phenyl 2-chlorobenzenecarbothioate Structure

S-phenyl 2-chlo...

p-tolylmethanol Structure

p-tolylmethanol

Thiophenol Structure

~85%

S-phenyl 4-methylbenzenecarbothioate Structure

S-phenyl 4-meth...