Amine compounds are ubiquitous in natural products as well as in bioactive materials and medicines. Although various methods for the preparation of amines have been studied, the direct addition of N-H bond to α, β-unsaturated olefins is one of the most attractive processes in terms of efficiency and atom-economy. Transition metal catalysis plays a crucial role in the development of amine conjugate addition reactions to electron-deficient olefins. Herein, we describe an efficient NHC-Cu catalyst system for the conjugate addition of a variety of aniline to activated alkenes. Amine additions are carried out in the presence of a mixture of 7 mol % CuCl, imidazolium salts as a precursor of NHC, KO<i>t</i>-Bu and aniline, generating NHC-Cu-NHPh <i>in situ</i>. Various olefins including a cyanide, ketone and ester group can be applied to this transformation, affording the amine products with up to 95% yield.

Amine conjugate addition to α,β-unsaturated olefins promoted by NHC-Cu catalyst

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.