Rhodium(iii)-catalyzed mild and regioselective dearomative spirocyclization of 2-aryl-3-nitrosoindoles with alkynes

Abstract

Herein, we develop a Rh(III)-catalyzed intermolecular regioselective dearomative spirocyclization of 2-aryl-3-nitrosoindoles with alkynes, featuring the redox-neutral and atom-economic construction of spiroindoline-3-one oximes bearing a C2 spirocyclic quaternary carbon center under mild conditions. Both aryl alkyl alkynes and 1,3-diynes generally proceeded smoothly in the reaction with moderate to good regioselectivities. DFT calculations provided in-depth insights into the reaction mechanism and disclosed the origins of the regioselectivities.