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Catalytic Three-Component Coupling of Alkynes, Imines, and Organoboron Reagents


  • We thank the NIGMS (GM063755), the NSF (CAREER CHE-0134704), Merck Research Laboratories, Pfizer, Boehringer-Ingelheim, 3M, Johnson & Johnson, The Donors of the PRF, and MIT for generous financial support. NSF grants CHE-9809061 and DBI-9729592 and NIH grant 1S10RR13886-01 provided partial support for the MIT Department of Chemistry Instrumentation Facility (DCIF).


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An unusual degree of functional group compatibility for imine addition reactions was observed in the assembly of allylic amines from alkynes, imines, and organoboron reagents (boronic acids or boranes) by using a catalyst derived from [Ni(cod)2] and (c-C5H9)3P—this catalytic three-component process (see scheme) is tolerant of ketones, esters, and hydroxylic solvents.