Modification of [2.2]paracyclophane through cobalt-catalyzed ortho-C–H allylation and acyloxylation

Abstract

It is non-trivial to access 4,5-disubstituted [2.2]paracyclophanes by directed C–H functionalization, due to their steric hindrance. Here we reported the first cobalt-catalyzed C–H functionalization of [2,2]paracyclophanes assisted by an 8-aminoquinoline directing group. A broad range of 4,5-disubstituted [2.2]paracyclophanes were prepared via cobalt-catalyzed C–H allylation and acyloxylation of the sterically demanding ortho-C–H bond. The reactions involve the use of an inexpensive cobalt salt as the catalyst and show high functional group tolerance, gram-scale synthesis, and diverse synthetic transformations.