Journal article

The modular synthesis of sulfondiimidoyl fluorides and their application to sulfondiimidamide and sulfondiimine synthesis

Abstract:: A modular synthesis of sulfondiimidoyl fluorides - the double aza-analogues of sulfonyl fluorides - allowing variation of the carbon and both nitrogen-substituents is reported. The chemistry uses readily available organometallic reagents, commercial sulfinylamines, simple electrophiles, and N-fluorobenzenesulfonimide (NFSI), as the starting materials. The reactions are broad in scope, efficient, and scalable. We show that the sulfondiimidoyl fluoride products can be combined with amines to provide sulfondiimidamides, and with organolithium reagents to provide sulfondiimines, and that reactivity in these transformations can be modulated by variation of the N-substituents.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Ding, M., Bell, C., & Willis, M. C. (2024). The modular synthesis of sulfondiimidoyl fluorides and their application to sulfondiimidamide and sulfondiimine synthesis. Angewandte Chemie International Edition, 63(38).

MLA Style

Ding, M., et al. “The Modular Synthesis of Sulfondiimidoyl Fluorides and Their Application to Sulfondiimidamide and Sulfondiimine Synthesis.” Angewandte Chemie International Edition, vol. 63, no. 38, Wiley, 2024.

Chicago Style

Ding, M, C Bell, and MC Willis. 2024. “The Modular Synthesis of Sulfondiimidoyl Fluorides and Their Application to Sulfondiimidamide and Sulfondiimine Synthesis.” Angewandte Chemie International Edition 63 (38).
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Files:: Ding_et_al_2024_The_modular_synthesis.pdf

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Publisher copy:: 10.1002/anie.202409240

Authors

+ Ding, M More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author

+ Bell, C More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author

+ Willis, MC More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Oxford college:: Lincoln College
Role:: Author
ORCID:: 0000-0002-0636-6471

Publisher:: Wiley
Journal:: Angewandte Chemie International Edition More from this journal
Volume:: 63
Issue:: 38
Article number:: e202409240
Publication date:: 2024-08-19
Acceptance date:: 2024-06-24
DOI:: 10.1002/anie.202409240
EISSN:: 1521-3773
ISSN:: 1433-7851

Language:: English
Keywords:: sulfur

SuFEx

synthetic methods

electrophiles
Pubs id:: 2009906
Local pid:: pubs:2009906
Deposit date:: 2024-06-24

Terms of use

Copyright holder:: Ding et al.
Copyright date:: 2024
Rights statement:: © 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

Licence:: CC Attribution (CC BY)

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