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Nickel-Catalyzed Deaminative Cyanation: Nitriles and One-Carbon Homologation from Alkyl Amines

Jianyu Xu, J. Cameron Twitty and Mary P. Watson*

*Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email: mpwatsonudel.edu

J. Xu, J. C. Twitty, M. P. Watson, Org. Lett., 2021, 23, 6242-6245.

DOI: 10.1021/acs.orglett.1c01959


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Abstract

A nickel-catalyzed deaminative cyanation of Katritzky pyridinium salts with Zn(CN)2 enables the conversion of primary alkyl amines to alkyl nitriles in good yields. The reaction tolerates diverse functional groups and heterocycles. The conversion of 2 Katritzky pyridinium salts is accompanied with partial inversion at the stereocenter consistent with formation of an alkyl radical intermediate.

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Key Words

cyanation


ID: J54-Y2021