Nickel-catalyzed asymmetric reductive cross-coupling between heteroaryl iodides and α-chloronitriles

Abstract

Ni-catalyzed asymmetric reductive cross-coupling provides an attractive and powerful means to access tertiary stereocenters. However these methods had previously been limited to benzylic alkyl partners and were not amenable to heterocyclic substrates. To expand the utility of this class of reactions, the Ni-catalyzed asymmetric cross-electrophile 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 under mild conditions enabled by a novel ligand scaffold. The products can be derivatized to a range of synthetically useful functionality.

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