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An Electrophilic Trifluoromethylthiolation of Silylenol Ethers and β ‐Naphthols with Diethylaminosulfur Trifluoride and (Trifluoromethyl)trimethylsilane
Author(s) -
Saravanan Perumal,
Anbarasan Pazhamalai
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800366
Subject(s) - chemistry , trimethylsilane , electrophile , moiety , trifluoromethyl , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , alkyl
An efficient and general trifluoromethylthiolation of silylenol ethers and β ‐naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF 3 TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α ‐trifluoromethylthiolated carbonyl compounds and β ‐naphthols in good yields. Important features of this method include wide functional group tolerance and use of readily available DAST/CF 3 TMS. Potential of the methodology was demonstrated via the synthesis of α ‐trifluoromethylthiolated (+)‐4‐cholesten‐3‐one and naphthoquinone.