Sulfur–Phenolate Exchange: SuFEx‐Derived Dynamic Covalent Reactions and Degradation of SuFEx Polymers

The products of the SuFEx reaction between sulfonimidoyl fluorides and phenols, sulfonimidates, are shown to display dynamic covalent chemistry with other phenols. This reaction was shown to be enantiospecific, finished in minutes at room temperature in high yields, and useful for both asymmetric sy...

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Bibliographic Details
Published in:Angewandte Chemie 2022-09, Vol.134 (36), p.n/a
Main Authors: Chao, Yang, Krishna, Akash, Subramaniam, Muthusamy, Liang, Dong‐Dong, Pujari, Sidharam P., Sue, Andrew C.‐H., Li, Guanna, Miloserdov, Fedor M., Zuilhof, Han
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Chemical synthesis
Chemistry
Click Chemistry
Enantiospecific Suphenex
Kinetics
Phenols
Polymers
Reaction Mechanisms
Room temperature
Sulfur
Sulfur–Phenolate Exchange
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Summary:The products of the SuFEx reaction between sulfonimidoyl fluorides and phenols, sulfonimidates, are shown to display dynamic covalent chemistry with other phenols. This reaction was shown to be enantiospecific, finished in minutes at room temperature in high yields, and useful for both asymmetric synthesis and sustainable polymer production. Its wide scope further extends the usefulness of SuFEx and related click chemistries. A sulfur(VI)–phenolate exchange (SuPhenEx) reaction between sulfonimidates and phenols has been shown to generate new sulfonimidates that undergo dynamic covalent reactions with other phenols. The fast, high‐yielding, and enantiospecific reactions are useful for both asymmetric synthesis and the degradation of SuFEx polymers. The wide scope of the reaction extends the usefulness of SuFEx and related click reactions.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202207456