Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies

Stephen R. Sardini, Alison L. Lambright, Grace L. Trammel, Humair M. Omer, Peng Liu*, M. Kevin Brown*

*University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260; Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States, Email: pengliupitt.edu, brownmkbindiana.edu

S. R. Sardini, A. L. Lambright, G. L. Trammel, H. M. Omer, P. Liu, M. K. Brown, J. Am. Chem. Soc., 2019, 141, 9391-9400.

DOI: 10.1021/jacs.9b03991

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Abstract

A Ni-catalyzed arylboration converts substituted alkenes, aryl bromides, and diboron reagents to products that contain a tertiary or quaternary carbon and a synthetically versatile carbon-boron bond with control of stereoselectivity and regioselectivity. In addition, the method is useful for the synthesis of saturated nitrogen heterocycles.

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Key Words

arylation, borylation, multicomponent reactions

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ID: J48-Y2019