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Iridium-catalyzed reductive Strecker reaction for late-stage amide and lactam cyanation

Abstract:

A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substituti...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

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Publisher copy:
10.1002/ange.201612367

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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Author
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Funding agency for:
de Arriba, ALF
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Funding agency for:
Sonawane, M
Publisher:
Wiley Publisher's website
Journal:
Angewandte Chemie Journal website
Volume:
129
Issue:
13
Pages:
3709-3713
Publication date:
2017-02-24
Acceptance date:
2017-01-10
DOI:
EISSN:
1521-3757
ISSN:
0044-8249
Pubs id:
pubs:718657
URN:
uri:d504ace3-c362-4c64-a8cc-f9dfba317fad
UUID:
uuid:d504ace3-c362-4c64-a8cc-f9dfba317fad
Local pid:
pubs:718657
Paper number:
13

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