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: michael.clift
abbvie.com
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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Abstract
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
