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. 2015 Aug 26;137(33):10480-3.
doi: 10.1021/jacs.5b06466. Epub 2015 Aug 13.

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles

Nathaniel T Kadunce  1 , Sarah E Reisman  1
Affiliations

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles

Nathaniel T Kadunce et al. J Am Chem Soc. .

Abstract

A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild conditions at room temperature and precludes the need to pregenerate organometallic nucleophiles.

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Figures

Scheme 1
Scheme 1
Transition metal-catalyzed cross-coupling reactions of α-cyano electrophiles.
Scheme 2
Scheme 2
Derivatization of α,α-disubstituted nitriles.
Scheme 3
Scheme 3
Mechanistic experiments.
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