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Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes

Poremba, Kelsey E. and Kadunce, Nathaniel T. and Suzuki, Naoyuki and Cherney, Alan H. and Reisman, Sarah E. (2017) Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes. Journal of the American Chemical Society, 139 (16). pp. 5684-5687. ISSN 0002-7863. PMCID PMC5851002. https://resolver.caltech.edu/CaltechAUTHORS:20170414-064225830

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Abstract

An asymmetric Ni-catalyzed reductive cross-coupling of (hetero)aryl iodides and benzylic chlorides has been developed to prepare enantioenriched 1,1-diarylalkanes. As part of these studies, a new chiral bioxazoline ligand, 4-heptyl-BiOX (L1), was developed in order to obtain products in synthetically useful yield and enantioselectivity. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, indoles, and piperidines.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.7b01705DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/jacs.7b01705PublisherSupporting Information
https://doi.org/10.1021/jacs.8b05247DOICorrection
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5851002PubMed CentralArticle
ORCID:
AuthorORCID
Poremba, Kelsey E.0000-0002-7446-257X
Kadunce, Nathaniel T.0000-0002-6566-9851
Cherney, Alan H.0000-0001-7440-6634
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2017 American Chemical Society. Received 17 February 2017. Published online 13 April 2017. We are grateful to Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We thank Dr. Leah Cleary for the initial preparation of ligands and Julie Hofstra for solving the structure of 3k (CCDC Deposition No. 1533022). Fellowship support was provided by the National Science Foundation (graduate research fellowship to K. E. P., Grant No. DGE-1144469), Amgen (Graduate Research Fellowship to N.T.K.), and Shionogi & Co., Ltd. (fellowship to N.S.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NIH (NIGMS R35GM118191-01; GM111805-01) is gratefully acknowledged.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
AmgenUNSPECIFIED
Shionogi & Co., Ltd.UNSPECIFIED
American Cancer SocietyUNSPECIFIED
Heritage Medical Research InstituteUNSPECIFIED
NIHR35GM118191-1
NIHGM111805-01
Issue or Number:16
PubMed Central ID:PMC5851002
Record Number:CaltechAUTHORS:20170414-064225830
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170414-064225830
Official Citation:Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes Kelsey E. Poremba, Nathaniel T. Kadunce, Naoyuki Suzuki, Alan H. Cherney, and Sarah E. Reisman Journal of the American Chemical Society 2017 139 (16), 5684-5687 DOI: 10.1021/jacs.7b01705
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76561
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:14 Apr 2017 18:17
Last Modified:21 Apr 2020 17:33

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