Quantification of the Activation Capabilities of Lewis/Brønsted Acid for Electrophilic Trifluoromethylthiolating Reagents

Summary of main observation and conclusion Electrophilic trifluoromethylthiolation has emerged as an important and efficient methodology for installing the SCF3 moiety onto an array of organic molecules. Due to the low reactivities of trifluoromethylthiolating reagents, these transformations often r...

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Bibliographic Details
Published in:Chinese journal of chemistry 2020-02, Vol.38 (2), p.130-134
Main Authors: Kang, Huiying, Zhou, Biying, Li, Man, Xue, Xiao‐Song, Cheng, Jin‐Pei
Format: Article
Language:English
Subjects:
Acidity
Activation
Organic chemistry
Reagents
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Summary:Summary of main observation and conclusion Electrophilic trifluoromethylthiolation has emerged as an important and efficient methodology for installing the SCF3 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. We have proposed a way to quantify the capabilities of various Lewis/Brønsted acids to activate electrophilic CF3S‐transfer reagents. A moderate correlation between the activation capability and Lewis acidity is observed.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201900412