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

Dong-Dong LiangDieuwertje E StreefkerkDaan JordaanJorden WagemakersJacob BaggermanHan Zuilhof
Published in: Angewandte Chemie (International ed. in English) (2020)
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.
Keyphrases
  • minimally invasive
  • room temperature
  • mass spectrometry
  • ionic liquid
  • capillary electrophoresis