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Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism
Author(s) -
Liang DongDong,
Streefkerk Dieuwertje E.,
Jordaan Daan,
Wagemakers Jorden,
Baggerman Jacob,
Zuilhof Han
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915519
Subject(s) - moiety , chemistry , mechanism (biology) , enantioselective synthesis , silylation , reaction mechanism , yield (engineering) , scope (computer science) , silicon , combinatorial chemistry , catalysis , organic chemistry , computational chemistry , materials science , computer science , philosophy , epistemology , metallurgy , programming language
SuFEx reactions, in which an S−F moiety reacts with a silyl‐protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high‐yielding, “Si‐free” and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products.