Trifluoromethyl-substituted sulfonium ylide: Rh-catalyzed carbenoid addition to trifluoromethylthioether

Yafei Liu; Xinxin Shao; Panpan Zhang; Long Lu; Qilong Shen

doi:10.1021/acs.orglett.5b01170

Trifluoromethyl-substituted sulfonium ylide: Rh-catalyzed carbenoid addition to trifluoromethylthioether

Org Lett. 2015 Jun 5;17(11):2752-5. doi: 10.1021/acs.orglett.5b01170. Epub 2015 May 14.

Authors

Yafei Liu¹, Xinxin Shao¹, Panpan Zhang¹, Long Lu¹, Qilong Shen¹

Affiliation

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

PMID: 25974253
DOI: 10.1021/acs.orglett.5b01170

Abstract

A highly efficient Rh-catalyzed carbenoid addition to trifluoromethylthioether for the formation of trifluoromethyl-substituted sulfonium ylide is described. The trifluoromethyl-substituted sulfonium ylide can act as an electrophilic trifluoromethylation reagent, as demonstrated by trifluoromethylation of β-ketoesters and aryl iodides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrocarbons, Fluorinated / chemistry*
Molecular Structure
Rhodium / chemistry*
Stereoisomerism
Sulfides / chemistry*

Substances

Hydrocarbons, Fluorinated
Sulfides
Rhodium