Catalyst-controlled regiodivergent 1,2-difunctionalization of alkenes with two carbon-based electrophiles

Regiodivergent catalysis provides an efficient strategic approach for the construction of architecturally different molecules from the same starting materials. In this field, the intermolecular regiodivergent 1,2-difunctionalization of alkenes with two electrophiles is still a challenging task. A ligand-controlled, nickel-catalyzed regiodivergent dicarbofunctionalization of alkenes using both aryl/vinyl halides and acetals as electrophiles under mild reductive reaction conditions has been accomplished. This study provides a general approach to accessing both beta-methoxyl esters and gamma-methoxyl esters from readily available acrylates, aryl halides and acetals. Experimental mechanistic evidence supports that the difference in regioselective outcomes is attributed to the ligand tuning the reactivity of the nickel catalyst, which results in different catalytic cycles operating for these two reaction conditions.

Automated summary

Regiodivergent catalysis is an efficient strategy for constructing architecturally different molecules from the same starting materials. This study achieved a ligand-controlled, nickel-catalyzed regiodivergent dicarbofunctionalization of alkenes using different electrophiles, providing a general approach for accessing diverse esters. The difference in regioselective outcomes is attributed to the ligand tuning the reactivity of the nickel catalyst, leading to different catalytic cycles.