Journal article
Base-activated latent heteroaromatic sulfinates as nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions
- Abstract:
- Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 2.3MB, Terms of use)
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- Publisher copy:
- 10.1002/anie.202109146
Authors
- Publisher:
- Wiley
- Journal:
- Angewandte Chemie International Edition More from this journal
- Volume:
- 60
- Issue:
- 41
- Pages:
- 22461-22468
- Publication date:
- 2021-09-08
- Acceptance date:
- 2021-07-30
- DOI:
- EISSN:
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1521-3773
- ISSN:
-
1433-7851
- Pmid:
-
34342107
- Language:
-
English
- Keywords:
- Pubs id:
-
1190410
- Local pid:
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pubs:1190410
- Deposit date:
-
2021-09-07
- ARK identifier:
Terms of use
- Copyright holder:
- Cook et al
- Copyright date:
- 2021
- Rights statement:
- © 2021 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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