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Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides

Joseph Derosa, Roman Kleinmans, Van T. Tran, Malkanthi K. Karunananda, Steven R. Wisniewski, Martin D. Eastgate, Keary M. Engle*

*Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States, Email: kearyscripps.edu

J. Derosa, R. Kleinmans, V. T. Tran, M. K. Karunananda, S. R. Wisniewski, M. D. Eastgate, K. M. Engle, J. Am. Chem. Soc., 2018, 140, 17878-17883.

DOI: 10.1021/jacs.8b11942 (free Supporting Information)


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Abstract

A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters delivers the desired 1,2-diarylated products with excellent regiocontrol. The reaction is enabled by an electron-deficient olefin (EDO) ligand. Under optimized conditions, a wide range of amides derived from 3-butenoic acid, 4-pentenoic acid, and allyl amines are compatible substrates.


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Key Words

arylation, 1,4-addition, multicomponent reactions


ID: J48-Y2018