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

Angewandte Chemie
Dong-Dong LiangHan Zuilhof

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.

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Citations

May 20, 2020·Chemistry : a European Journal·Stephanie GreedJames Adam Bull
Aug 17, 2020·Organic & Biomolecular Chemistry·Priscilla Mendonça Matos, Robert A Stockman
Nov 17, 2020·Angewandte Chemie·Xingliang NieSaihu Liao
Mar 5, 2021·Chemical Reviews·Bauke AlbadaFloris van Delft
May 7, 2021·Chemical Communications : Chem Comm·Yiyuan ZhangHongtao Xu
Jun 15, 2021·ACS Catalysis·Cayo LeeNicholas D Ball
Oct 27, 2020·The Journal of Organic Chemistry·Jorge EscorihuelaHan Zuilhof
Aug 18, 2021·Nature Chemistry·Suhua LiK Barry Sharpless

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

Click
Gaussian

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