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Reductive hydroxymethylation of 4‐heteroarylpyridines

Abstract:
The activation of pyridinium salts with electron‐withdrawing heterocycles enables an iridium‐catalyzed reductive hydroxymethylation reaction to proceed smoothly, facilitating the preparation of useful 3D heteroaryl‐substituted functionalized piperidines. The methodology is used to prepare 3‐hydroxymethylated analogues of pharmaceutical agents. Mechanistically, formaldehyde acts as both a hydride donor and the electrophile, leading to the formation of two new carbon–hydrogen bonds and one new carbon–carbon bond under relatively mild conditions.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1002/chem.202000060

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More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Wolfson College
Role:
Author
More by this author
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Magdalen College
Role:
Author
Publisher:
Wiley Publisher's website
Journal:
Chemistry: A European Journal Journal website
Volume:
26
Issue:
9
Pages:
1963-1967
Publication date:
2020-01-30
Acceptance date:
2020-01-07
DOI:
EISSN:
1521-3765
ISSN:
0947-6539
Language:
English
Keywords:
Pubs id:
1083676
Local pid:
pubs:1083676
Deposit date:
2020-01-28

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