Journal article

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides

Abstract:: A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation succesfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated.

Publication status:: Published

Peer review status:: Peer reviewed

Actions

Email

Email this record

Send the bibliographic details of this record to your email address.

Your Email
Please enter the email address that the record information will be sent to.

-
Your message (optional)
Please add any additional information to be included within the email.
Cite

Cite this record

APA Style

Davies, A., Curto, J., Bagley, S., & Willis, M. (2016). One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides. Chemical Science.

MLA Style

Davies, A., et al. “One-Pot Palladium-Catalyzed Synthesis of Sulfonyl Fluorides from Aryl Bromides.” Chemical Science, Royal Society of Chemistry, 2016.

Chicago Style

Davies, A, J Curto, S Bagley, and M Willis. 2016. “One-Pot Palladium-Catalyzed Synthesis of Sulfonyl Fluorides from Aryl Bromides.” Chemical Science.
Share
Print

Access Document

Files:: Willis et al, One-pot palladium-catalyzed synthesis of sulfony...

(Preview, Version of record, pdf, 732.3KB, Terms of use)

Publisher copy:: 10.1039/C6SC03924C

Authors

+ Davies, A More by this author

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

+ Curto, J More by this author

Role:: Author

+ Bagley, S More by this author

Role:: Author

+ Willis, M More by this author

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

Publisher:: Royal Society of Chemistry
Journal:: Chemical Science More from this journal
Publication date:: 2016-10-01
Acceptance date:: 2016-10-02
DOI:: 10.1039/C6SC03924C
ISSN:: 2041-6539

Pubs id:: pubs:647881
UUID:: uuid:84a8c85d-2e17-4e3b-9617-f28b863d31dc
Local pid:: pubs:647881
Source identifiers:: 647881
Deposit date:: 2016-10-04

Terms of use

Copyright holder:: Royal Society of Chemistry
Copyright date:: 2016
Notes:: © The Royal Society of Chemistry 2016. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Licence:: CC Attribution (CC BY)

Views and Downloads

About views and downloads

If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP