The SuFEx reaction is one of the most promising novel reactions, displaying many of the characteristics of 'click reactions'. Characteristically, a silyl-protected phenol (Ar-O-SiR3) reacts with high efficiency under mild reaction conditions with a S-F bond in a range of sulfur-based compounds, forming both an Aryl-O-S bond in a novel functional molecule and a R3Si-F bond. While highly successful in a range of applications, ranging from biological to materials chemistry, the mechanism of this reaction is still highly unclear. In the current paper we outline the role of the silicon-based protection groups, the scope of the reaction, and outline the mechanism by investigating the kinetics, enantioselectivity and study of substituent effects by both experimental and quantum-chemical investigations.

SuFEx reactions and the role of silicon: Scope, kinetics, enantioselectivity and mechanism

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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