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Published August 2, 2019 | Accepted Version + Supplemental Material
Journal Article Open

Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis

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.

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.

Attached Files

Accepted Version - nihms-1039343.pdf

Supplemental Material - cs9b01785_si_001.pdf

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Created:
August 19, 2023
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October 20, 2023