Arylcyanation of Norbornene and Norbornadiene Catalyzed by Nickel

Abstract Aryl cyanides add to norbornene and norbornadiene under nickel catalysis to give (2R*,3S*)-3-aryl-2-cyanobicyclo[2.2.1]heptanes and (2R*,3S*)-3-aryl-2-cyanobicyclo[2.2.1]hept-5-enes in good yields with a general substrate scope. On the other hand, the reaction of an aryl cyanide with triethoxy(vinyl)silane gives a Heck-type arylation product, suggesting the arylnickelation pathway in the catalytic cycle.