Citation: Shen Zhao, Qing Fa Zhou, Jia Zhi Liu, Wei Fang Tang, Tao Lu. Tributylphosphine-catalyzed reaction of ethanethiol with alkynyl ketones[J]. Chinese Chemical Letters, ;2011, 22(4): 397-400. doi: 10.1016/j.cclet.2010.11.007 shu

Tributylphosphine-catalyzed reaction of ethanethiol with alkynyl ketones

Shen Zhao ^a, ,
Qing Fa Zhou ^a ,
Jia Zhi Liu ^a ,
Wei Fang Tang ^a ,
Tao Lu ^a,b

a Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China;
b Key Laboratory of Drug Quality Control and Pharmacovigilance, China Pharmaceutical University, Ministry of Education, Nanjing 210009, China

Received Date: 9 July 2010

Fund Project: We are grateful for the financial support from National Natural Science Foundation of China (No. 30973609).

A stereoselective and effective method for the synthesis of vinyl thioethers has been developed. This method is based on the Michael addition of ethanethiol to various alkynyl ketones using 10 mol% of tributylphosphine as catalyst. Most of alkynyl ketones react with ethanethiol in this system to yield mainly Z-isomer of vinyl thioether adducts, only in one case mainly E-isomer of vinyl thioether adducts was observed.
- Tributylphosphine,
- Synthesis,
- Alkynyl ketones,
- Michael addition,
- Vinyl thioether
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