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

Kadunce, Nathaniel T. and Reisman, Sarah E. (2015) Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles. Journal of the American Chemical Society, 137 (33). pp. 10480-10483. ISSN 0002-7863. PMCID PMC5066588. doi:10.1021/jacs.5b06466. https://resolver.caltech.edu/CaltechAUTHORS:20150917-141844097

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jacs.5b06466DOIArticle
http://pubs.acs.org/doi/suppl/10.1021/jacs.5b06466PublisherSupporting Information
http://resolver.caltech.edu/CaltechAUTHORS:20160302-080558393Related ItemConference Paper
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5066588/PubMed CentralArticle
ORCID:
AuthorORCID
Kadunce, Nathaniel T.0000-0002-6566-9851
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2015 American Chemical Society. Received: June 22, 2015; Published: August 9, 2015. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Dr. Alan Cherney and Robert Scanes for helpful discussions, and Dr. Michael Takase and Julie Hofstra for X-ray crystallographic structure determination. S.E.R. is a Camille Dreyfus Teacher-Scholar and an American Cancer Society Research Scholar. Financial support from NIH (GM111805-01), Amgen, Novartis, and Eli Lilly is gratefully acknowledged. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHGM111805-01
AmgenUNSPECIFIED
NovartisUNSPECIFIED
Eli LillyUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Issue or Number:33
PubMed Central ID:PMC5066588
DOI:10.1021/jacs.5b06466
Record Number:CaltechAUTHORS:20150917-141844097
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150917-141844097
Official Citation:Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles Nathaniel T. Kadunce and Sarah E. Reisman Journal of the American Chemical Society 2015 137 (33), 10480-10483 DOI: 10.1021/jacs.5b06466
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60304
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:17 Sep 2015 21:41
Last Modified:24 May 2022 22:37

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