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Formal α-Allylation of Primary Amines by a Dearomative, Palladium-Catalyzed Umpolung Allylation of N-(Aryloxy)imines

Luis M. Mori-Quiroz, Shrikant S. Londhe and Michael D. Clift*

*Department of Chemistry, The University of Kansas, 1140 Gray-Little Hall, 1567 Irving Hill Road, Lawrence, Kansas 66045, United States, Email:

L. M. Mori-Quiroz, S. S. Londhe, M. D. Clift, J. Org. Chem., 2020, 85, 14827-14846.

DOI: 10.1021/acs.joc.0c01020

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Readily accessible N-(aryloxy)imines undergo efficient allylation to afford a wide range of homoallylic primary amines following hydrolytic workup. Deprotonation of N-(aryloxy)imines generates a delocalized 2-azaallyl anion-type nucleophile that engages in dearomative unselective allylation followed by [1,3]- or concerted [3,3]-sigmatropic shifts to provide the desired products.

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reaction progress followed by NMR

Key Words

homoallylic amines, Tsuji-Trost reaction

ID: J42-Y2020