Approach Toward Stereoselective α-Arylation by Pd/Cu-Catalyzed Arylboration of Electron Deficient Alkenes

Abstract

Palladium-catalyzed cross coupling of enolates—α-arylation—is an established method for chemical synthesis. A major challenge in the field is control of stereochemistry for the α-carbon. This is typically due to facile epimerization under the basic reaction conditions for α-arylation. In this study, an alternative approach is presented that involves the Pd/Cu-catalyzed arylboration of electron deficient alkenes. The products are generated with high levels of diastereoselectivity for a broad range of substitution patterns. Enantioselective variants are also presented in addition to product derivatizations.