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Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes To Form Hindered Secondary Alcohols

Kevin J. Garcia, Michael M. Gilbert, Daniel J. Weix*

*Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States, Email: dweixwisc.edu

K. J. Garcia, M. M. Gilbert, D. J. Weix, J. Am. Chem. Soc., 2019, 141, 1823-1827.

DOI: 10.1021/jacs.8b13709 (free Supporting Information)



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Abstract

Simple nickel complexes of bipyridine and PyBox catalyze the addition of aryl halides to both aromatic and aliphatic aldehydes using zinc metal as the reducing agent. This convenient approach tolerates acidic functional groups that are not compatible with Grignard reactions, yet sterically hindered substrates still couple in high yield.

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proposed mechanism



Key Words

arylation, zinc


ID: J48-Y2019