Journal article
Synthetic exploration of sulfinyl radicals using sulfinyl sulfones
- Abstract:
- Sulfinyl radicals – one of the fundamental classes of S-centered radicals – have eluded synthetic application in organic chemistry for over 60 years, despite their potential to assemble valuable sulfoxide compounds. Here we report the successful generation and use of sulfinyl radicals in a dual radical addition/radical coupling with unsaturated hydrocarbons, where readily-accessed sulfinyl sulfones serve as the sulfinyl radical precursor. The strategy provides an entry to a variety of previously inaccessible linear and cyclic disulfurized adducts in a single step, and demonstrates tolerance to an extensive range of hydrocarbons and functional groups. Experimental and theoretical mechanistic investigations suggest that these reactions proceed through sequential sulfonyl and sulfinyl radical addition.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, 1.3MB, Terms of use)
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- Publisher copy:
- 10.1038/s41467-021-25593-5
Authors
- Publisher:
- Springer Nature
- Journal:
- Nature Communications More from this journal
- Volume:
- 12
- Article number:
- 5244
- Publication date:
- 2021-09-02
- Acceptance date:
- 2021-08-13
- DOI:
- EISSN:
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2041-1723
- Pmid:
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34475405
- Language:
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English
- Keywords:
- Pubs id:
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1195503
- Local pid:
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pubs:1195503
- Deposit date:
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2021-10-13
Terms of use
- Copyright holder:
- Wang et al.
- Copyright date:
- 2021
- Rights statement:
- Copyright © 2021 The Author(s). This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
- Licence:
- CC Attribution (CC BY)
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