Structure–Reactivity Relationship of Trifluoromethanesulfenates: Discovery of an Electrophilic Trifluoromethylthiolating Reagent

A family of electrophilic trifluoromethanesulfenates was prepared. Structure–reactivity relationship studies showed that the substituted groups on the aryl ring of the trifluoromethylthiolating reagent did not have an obvious influence on their reactivities. A simplified electrophilic trifluoromethy...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-03, Vol.80 (6), p.3012-3021
Main Authors: Shao, Xinxin, Xu, Chunfa, Lu, Long, Shen, Qilong
Format: Article
Language:English
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Summary:A family of electrophilic trifluoromethanesulfenates was prepared. Structure–reactivity relationship studies showed that the substituted groups on the aryl ring of the trifluoromethylthiolating reagent did not have an obvious influence on their reactivities. A simplified electrophilic trifluoromethylthiolating reagent 1c was then identified that can react with a wide range of nucleophiles such as Grignard reagents, arylboronic acids, alkynes, indoles, β-ketoesters, oxindoles, and sodium sulfinates under mild reaction conditions. A variety of functional groups were tolerated under these conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502645m