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).


original image

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.