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Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles

Alan H. Cherney and Sarah E. Reisman*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: reismancaltech.edu

A. H. Cherney, S. E. Reisman, J. Am. Chem. Soc., 2014, 136, 14365-14366.

DOI: 10.1021/ja508067c (free Supporting Information)


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Abstract

A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope can be converted under mild reaction conditions without pregeneration of organometallic reagents and the regioselectivity issues commonly associated with allylic arylation.

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Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides

N. Suzuki, J. L. Hofstra, K. E. Poremba, S. E. Reisman, Org. Lett., 2017, 19, 2150-2153.


Key Words

vinylation, benzylation, manganese


ID: J48-Y2014