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Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides

Abstract:

Pyridine rings are ubiquitous in drug molecules; however, the pre-eminent reaction used to form carbon–carbon bonds in the pharmaceutical industry, the Suzuki–Miyaura cross-coupling reaction, often fails when applied to these structures. This phenomenon is most pronounced in 2-substituted pyridines, and results from the difficulty in preparing, the poor stability of, and low efficiency in reactions of pyridine-2-boronates. We demonstrate that by replacing these boronates with pyridine-2-sulfi...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Publisher's version

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Publisher copy:
10.1039/C7SC00675F

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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Department:
Lincoln College
Role:
Author
Pfizer, Inc. More from this funder
Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Chemical Science Journal website
Volume:
8
Issue:
6
Pages:
4437-4442
Publication date:
2017-04-28
Acceptance date:
2017-04-11
DOI:
EISSN:
2041-6539
ISSN:
2041-6520
Pubs id:
pubs:688985
URN:
uri:3b6b3060-5c07-490b-84b0-63e100d46266
UUID:
uuid:3b6b3060-5c07-490b-84b0-63e100d46266
Local pid:
pubs:688985
Paper number:
6

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