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Enantioselective, nickel-catalyzed Suzuki cross-coupling of quinolinium ions.

ABSTRACT: Quinolinium ions are engaged in an asymmetric, Ni-catalyzed Suzuki cross-coupling to yield 2-aryl- and 2-heteroaryl-1,2-dihydroquinolines. Key to the development of this method is the use of a Ni(II) precatalyst that activates without the need for strong reductants or high temperatures. The Ni-iminium activation mode is demonstrated as an exceptionally mild pathway to generate enantioenriched products from racemic starting materials.

SUBMITTER: Shields JD

PROVIDER: S-EPMC3924560 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Enantioselective, nickel-catalyzed Suzuki cross-coupling of quinolinium ions.

Shields Jason D JD Ahneman Derek T DT Graham Thomas J A TJ Doyle Abigail G AG

Organic letters 20131126 1

Quinolinium ions are engaged in an asymmetric, Ni-catalyzed Suzuki cross-coupling to yield 2-aryl- and 2-heteroaryl-1,2-dihydroquinolines. Key to the development of this method is the use of a Ni(II) precatalyst that activates without the need for strong reductants or high temperatures. The Ni-iminium activation mode is demonstrated as an exceptionally mild pathway to generate enantioenriched products from racemic starting materials. ...[more]

PMID: 24279380

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