Cascade Pd-Catalyzed Intermolecular N-Arylation/Intramolecular Alkene Carboamination Reactions for the Synthesis of
Matthew R Culberson1, Siqi Dong1, John P Wolfe1
1Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.
Abstract:
The palladium-catalyzed cross-coupling of 2-allylanilines with 1-bromo-2-chlorobenzene derivatives provides dihydroindoloindoles in moderate to good yield with up to 15:1 dr. The transformations involve initial Pd-catalyzed N-arylation to generate a substituted diphenylamine derivative, followed by intramolecular Pd-catalyzed carboamination of the alkene via an azapalladabenzocyclobutene intermediate to generate the tetracyclic products. The scope, mechanism, and stereocontrol of these reactions is described.
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