Silicon-Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism

Dong Dong Liang, Dieuwertje E. Streefkerk, Daan Jordaan, Jorden Wagemakers, Jacob Baggerman, Han Zuilhof*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7494-7500
JournalAngewandte Chemie - International Edition
Volume59
Issue number19
Early online date11 Mar 2020
DOIs
Publication statusPublished - 4 May 2020

Keywords

  • enantioselectivity
  • kinetics
  • reaction mechanisms
  • SuFEx

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