Asymmetric borylative coupling of vinylazaarenes and ketones catalyzed by a copper(i) complex

Abstract

Azaarenes are attractive structural units widely found in chiral pharmaceuticals, agrochemicals, and biologically active natural products. An ongoing strategy has been the construction of new chiral molecules containing azaarenes by virtue of the electron-deficient properties of azaarenes. Herein, an asymmetric three-component coupling of vinylazaarenes, B2Pin2, and ketones was achieved in the presence of a chiral copper(I) catalyst. The reaction favored a broad substrate scope of either vinylazaarenes or ketones. High enantioselectivity was observed in this reaction together with moderate diastereoselectivity, attributable to the relatively small difference of steric repulsion between two proposed transition states. Finally, the synthetic utilities of the product were demonstrated by several beneficial transformation reactions.