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

Yang Chao; Akash Krishna; Muthusamy Subramaniam; Dong Dong Liang; Sidharam P. Pujari; Andrew C.H. Sue; Guanna Li; Fedor M. Miloserdov; Han Zuilhof

doi:10.1002/anie.202207456

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

Yang Chao, Akash Krishna, Muthusamy Subramaniam, Dong Dong Liang, Sidharam P. Pujari, Andrew C.H. Sue, Guanna Li, Fedor M. Miloserdov, Han Zuilhof^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

26 Citations (Scopus)

Abstract

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.

Original language	English
Article number	e202207456
Journal	Angewandte Chemie - International Edition
Volume	61
Issue number	36
DOIs	https://doi.org/10.1002/anie.202207456
Publication status	Published - 5 Sept 2022

Keywords

Click Chemistry
Enantiospecific Suphenex
Kinetics
Reaction Mechanisms
Sulfur–Phenolate Exchange

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10.1002/anie.202207456Licence: CC BY-NC-ND

https://edepot.wur.nl/577206Licence: CC BY-NC-ND

CCDC 2159142: Experimental Crystal Structure Determination
Chao, Y. (Creator), Krishna, A. (Creator), Subramaniam, M. (Creator), Liang, D. D. (Creator), Pujari, S. P. (Creator), Sue, A. C. H. (Creator), Li, G. (Creator), Miloserdov, F. M. (Creator) & Zuilhof, H. (Creator), Tianjin University, 16 Mar 2022
DOI: 10.5517/ccdc.csd.cc2bgrrb
Dataset
CCDC 2159141: Experimental Crystal Structure Determination
Chao, Y. (Creator), Krishna, A. (Creator), Subramaniam, M. (Creator), Liang, D. D. (Creator), Pujari, S. P. (Creator), Sue, A. C. H. (Creator), Li, G. (Creator), Miloserdov, F. M. (Creator) & Zuilhof, H. (Creator), Tianjin University, 16 Mar 2022
DOI: 10.5517/ccdc.csd.cc2bgrq9
Dataset
CCDC 2159137: Experimental Crystal Structure Determination
Chao, Y. (Creator), Krishna, A. (Creator), Subramaniam, M. (Creator), Liang, D. D. (Creator), Pujari, S. P. (Creator), Sue, A. C. H. (Creator), Li, G. (Creator), Miloserdov, F. M. (Creator) & Zuilhof, H. (Creator), Tianjin University, 16 Mar 2022
DOI: 10.5517/ccdc.csd.cc2bgrl5
Dataset

Cite this

@article{a2c0ba10d0e648fc8d0e9501906fcea9,

title = "Sulfur–Phenolate Exchange: SuFEx-Derived Dynamic Covalent Reactions and Degradation of SuFEx Polymers",

abstract = "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.",

keywords = "Click Chemistry, Enantiospecific Suphenex, Kinetics, Reaction Mechanisms, Sulfur–Phenolate Exchange",

author = "Yang Chao and Akash Krishna and Muthusamy Subramaniam and Liang, {Dong Dong} and Pujari, {Sidharam P.} and Sue, {Andrew C.H.} and Guanna Li and Miloserdov, {Fedor M.} and Han Zuilhof",

year = "2022",

month = sep,

day = "5",

doi = "10.1002/anie.202207456",

language = "English",

volume = "61",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

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number = "36",

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TY - JOUR

T1 - Sulfur–Phenolate Exchange

T2 - SuFEx-Derived Dynamic Covalent Reactions and Degradation of SuFEx Polymers

AU - Chao, Yang

AU - Krishna, Akash

AU - Subramaniam, Muthusamy

AU - Liang, Dong Dong

AU - Pujari, Sidharam P.

AU - Sue, Andrew C.H.

AU - Li, Guanna

AU - Miloserdov, Fedor M.

AU - Zuilhof, Han

PY - 2022/9/5

Y1 - 2022/9/5

N2 - 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.

AB - 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.

KW - Click Chemistry

KW - Enantiospecific Suphenex

KW - Kinetics

KW - Reaction Mechanisms

KW - Sulfur–Phenolate Exchange

U2 - 10.1002/anie.202207456

DO - 10.1002/anie.202207456

M3 - Article

C2 - 35819248

AN - SCOPUS:85137079817

SN - 1433-7851

VL - 61

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 36

M1 - e202207456

ER -

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

Abstract

Keywords

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Datasets

CCDC 2159142: Experimental Crystal Structure Determination

CCDC 2159141: Experimental Crystal Structure Determination

CCDC 2159137: Experimental Crystal Structure Determination

Cite this