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Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis

DeLano, Travis J. and Reisman, Sarah E. (2019) Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis. ACS Catalysis, 9 (8). pp. 6751-6754. ISSN 2155-5435. PMCID PMC7190267. https://resolver.caltech.edu/CaltechAUTHORS:20190625-112222475

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Abstract

An electrochemically driven enantioselective nickel-catalyzed reductive cross-coupling of alkenyl bromides and benzyl chlorides is reported. The reaction forms products bearing allylic stereogenic centers with good enantioselectivity under mild conditions in an undivided cell. Electrochemical activation and turnover of the catalyst mitigate issues posed by metal powder reductants. This report demonstrates that enantioselective Ni-catalyzed cross-electrophile couplings can be driven electrochemically.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acscatal.9b01785DOIArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/pmc7190267/PubMed CentralArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2019 American Chemical Society. Received: May 1, 2019; Revised: June 21, 2019; Published: June 25, 2019. We thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We thank Dr. Julie Hofstra for assistance with experimental design. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, T.J.D., Grant No. DGE-1144469). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01) is gratefully acknowledged. The authors declare no competing financial interest.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
Heritage Medical Research InstituteUNSPECIFIED
NIHR35GM118191-01
Subject Keywords:Nickel, electrochemistry, enantioselective, crosscoupling, asymmetric catalysis
Issue or Number:8
PubMed Central ID:PMC7190267
Record Number:CaltechAUTHORS:20190625-112222475
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20190625-112222475
Official Citation:Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis. Travis J. DeLano and Sarah E. Reisman. ACS Catalysis 2019 9 (8), 6751-6754. DOI: 10.1021/acscatal.9b01785
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:96697
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:25 Jun 2019 18:29
Last Modified:30 Apr 2020 20:28

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