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Palladium-catalyzed enolate arylation as a key C-C bond-forming reaction for the synthesis of isoquinolines.

Abstract:

The palladium-catalyzed coupling of an enolate with an ortho-functionalized aryl halide (an α-arylation) furnishes a protected 1,5-dicarbonyl moiety that can be cyclized to an isoquinoline with a source of ammonia. This fully regioselective synthetic route tolerates a wide range of substituents, including those that give rise to the traditionally difficult to access electron-deficient isoquinoline skeletons. These two synthetic operations can be combined to give a three-component, one-pot iso...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c5ob02320c

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Funding agency for:
Gatland, A
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Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Organic and Biomolecular Chemistry Journal website
Volume:
14
Issue:
3
Pages:
1065-1090
Publication date:
2015-12-03
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Source identifiers:
588834
Language:
English
Pubs id:
pubs:588834
UUID:
uuid:570b13c3-c8c5-4322-8044-73175680bfa0
Local pid:
pubs:588834
Deposit date:
2016-02-10

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