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.cliftabbvie.com
L. M. Mori-Quiroz, S. S. Londhe, M. D. Clift, J. Org. Chem., 2020, 85, 14827-14846.
see article for more reactions
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.
see article for more examples
reaction progress followed by NMR