Quantification of the Activation Capabilities of Lewis/Brønsted Acid for Electrophilic Trifluoromethylthiolating Reagents. Issue 2 (24th December 2019)

• Record Type: Journal Article
• Authors: Kang, Huiying; Zhou, Biying; Li, Man; Xue, Xiao‐Song; Cheng, Jin‐Pei
• Is Part Of: Chinese journal of chemistry. Volume 38:Issue 2(2020)
• Page Start: 130
• Page End: 134
• Publication Date: 2019-12-24
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201900412
• Languages: English
• ISSNs: 1001-604X

Abstract

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. Abstract : We have proposed a way to quantify the capabilities of various Lewis/Brønsted acids to activate electrophilic CF3 S‐transfer reagents. A moderate correlation between the activation capability and Lewis acidity is observed.