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A general copper-catalyzed synthesis of Ynamides from 1,2-dichloroenamides

Abstract:
Ynamides are accessed via copper-catalyzed coupling of Grignard or organozinc nucleophiles with chloroynamides, formed in situ from 1,2-dichloroenamides. The reaction exhibits a broad substrate scope, is readily scaled, and overcomes typical limitations in ynamide synthesis such as the use of ureas, carbamates, and bulky or aromatic amide derivatives. This modular approach contrasts with previous routes by installing both the N- and C-substituents of the ynamide as nucleophilic components.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.orglett.9b00971

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Jesus College
Role:
Author
ORCID:
0000-0002-4149-0494
Publisher:
American Chemical Society Publisher's website
Journal:
Organic letters Journal website
Volume:
21
Issue:
8
Pages:
2918-2922
Publication date:
2019-04-03
Acceptance date:
2019-03-26
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pmid:
30942600
Source identifiers:
991080
Language:
English
Keywords:
Pubs id:
pubs:991080
UUID:
uuid:545ccce8-f6fe-4902-b2e1-1ac54850466c
Local pid:
pubs:991080
Deposit date:
2019-05-17

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