We demonstrated here an efficient synthetic method of carbazole derivatives from readily available Narylnaphthalen-2-amines and quinone esters catalyzed by Brønsted acid. With this strategy, a series of carbazole derivatives were obtained in good to excellent yields (76 to >99) under mild conditions. Large scale reaction illustrated the synthetic utility of this protocol. Meanwhile, a series of C−N axially chiral carbazole derivatives were also constructed in moderate to good yields (36− 89% yield) with moderate to excellent atroposelectivities (44−94% ee) by using chiral phosphoric acid as a catalyst, which provides a novel strategy for the atroposelective construction of C−N axially chiral compounds and a new member of the C−N atropisomers.

A catalyst-free aza-Michael addition/C(sp3)-O bond formation tandem reaction of substituted amino ferrocenes with quinone esters was developed, which provided a green and efficient strategy for the construction of a C(sp3)-O bond from C(sp3)-H, and a series of N-ferrocene-substituted benzodihydrooxazoles were smoothly produced in moderate to excellent yields (up to >99% yield). The mechanism experiments showed that quinone esters performed as both substrate and oxidant. The salient features of this transformation include good functional group tolerance, broad substrate scope and mild conditions.