Enantioselective, nickel-catalyzed suzuki cross-coupling of quinolinium ions

Jason D. Shields; Derek T. Ahneman; Thomas J.A. Graham; Abigail G. Doyle

doi:10.1021/ol4031364

Enantioselective, nickel-catalyzed suzuki cross-coupling of quinolinium ions

Jason D. Shields, Derek T. Ahneman, Thomas J.A. Graham, Abigail G. Doyle

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

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.

Original language	English (US)
Pages (from-to)	142-145
Number of pages	4
Journal	Organic letters
Volume	16
Issue number	1
DOIs	https://doi.org/10.1021/ol4031364
State	Published - Jan 3 2014

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol4031364

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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.",

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AU - Ahneman, Derek T.

AU - Graham, Thomas J.A.

AU - Doyle, Abigail G.

PY - 2014/1/3

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AB - 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.

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Enantioselective, nickel-catalyzed suzuki cross-coupling of quinolinium ions

Abstract

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