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Quantification of the Activation Capabilities of Lewis/Brønsted Acid for Electrophilic Trifluoromethylthiolating Reagents †
Author(s) -
Kang Huiying,
Zhou Biying,
Li Man,
Xue XiaoSong,
Cheng JinPei
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900412
Subject(s) - chemistry , reagent , electrophile , lewis acids and bases , moiety , brønsted–lowry acid–base theory , combinatorial chemistry , catalysis , molecule , organic chemistry
Summary of main observation and conclusion Electrophilic trifluoromethylthiolation has emerged as an important and efficient methodology for installing the SCF 3 moiety onto an array of organic molecules. Due to the low reactivities of trifluoromethylthiolating reagents, these transformations often require activation through an exogenous Lewis/Brønsted acid. We report herein the quantification of the activation capabilities of Lewis/Brønsted acids for trifluoromethylthiolating reagents through computing the difference in trifluoromethylthio cation donor ability (Tt + DA) between the "activated” and “unactivated” reagent. A moderate correlation is found to exist between the activation capability and Lewis acidity.