Access to [4,3,1]-Bridged Carbocycles via Rhodium(III)-Catalyzed C-H Activation of 2-Arylindoles and Annulation with Quinone Monoacetals.

Reported herein is the Rh(III)-catalyzed annulation of N-unprotected 2-arylindoles with quinone monoacetals for the straightforward synthesis of [4,3,1]-bridged carbocycles with exclusive C(3) selectivity. Mechanistic studies, particularly deuterium-labeling experiments, suggest that the coupling likely proceeds via two-fold C-H activation with two-fold migratory insertion into the enone moieties.