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

Kadunce, Nathaniel T. (2015) Nickel-catalyzed asymmetric reductive cross-coupling between heteroaryl iodides and α-chloronitriles. In: 45th Western Regional Meeting of the American Chemical Society, November 6-8, 2015, San Marcos, CA.

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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.

Item Type:Conference or Workshop Item (Paper)
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Kadunce, Nathaniel T.0000-0002-6566-9851
Additional Information:© 2015 American Chemical Society.
Record Number:CaltechAUTHORS:20160302-080558393
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:64947
Deposited By: Tony Diaz
Deposited On:02 Mar 2016 17:16
Last Modified:03 Oct 2019 09:42

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