Published August 26, 2015
| Accepted Version + Supplemental Material
Journal Article
Open
Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles
- Creators
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Kadunce, Nathaniel T.
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Reisman, Sarah E.
Chicago
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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.
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.Attached Files
Accepted Version - nihms821011.pdf
Supplemental Material - ja5b06466_si_001.pdf
Supplemental Material - ja5b06466_si_002.pdf
Supplemental Material - ja5b06466_si_003.cif
Files
ja5b06466_si_002.pdf
Additional details
- PMCID
- PMC5066588
- Eprint ID
- 60304
- DOI
- 10.1021/jacs.5b06466
- Resolver ID
- CaltechAUTHORS:20150917-141844097
- NIH
- GM111805-01
- Amgen
- Novartis
- Eli Lilly
- Camille and Henry Dreyfus Foundation
- Created
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2015-09-17Created from EPrint's datestamp field
- Updated
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2022-05-24Created from EPrint's last_modified field