Nickel-Catalyzed Arylation/Lactonization Cascade Reactions for the Synthesis of Bicyclo[3.2.1]lactones

An experimental and theoretical investigation of the nickel-catalyzed arylative ring-opening/lactonization cascade reactions of oxabicyclic alkenes with aryl halides is reported. The reaction functionalized bicyclo[3.2.1]lactone products in good yields with complete regio- and stereoselectivity. The mechanism and origins of selectivity in the nickel-catalyzed cascade reaction were examined at the omega B97X-D/Def2-TZVPP level of theory.