Visible-light-induced reductive dearomatization of non-activated arenes is a very challenging transformation and remains in its infancy. Herein, we report a novel strategy to achieve a visible-light-induced spirocyclizative remote arylcarboxylation of non-activated arenes including naphthalenyl-and phenyl-bearing aromatics with CO 2 under mild conditions through a radical-polar crossover cascade (RPCC). This reductive dearomatization protocol rapidly delivers a broad range of spirocyclic and valuable carboxylic acid derivatives from readily accessible aromatic precursors with generally good regioselectivity and chemoselectivity.

Functional group metathesis has the potential to render mild reaction conditions for C–H functionalization. Protocols for the meta- and ortho-C–H iodination of aniline derivatives via formal C­(sp2)–H/C­(sp2)–I metathesis using 2-nitrophenyl iodides as mild iodinating reagents are reported herein. These protocols led to the production of a range of valuable iodinated aniline derivatives. These results demonstrate the potential of developing novel site-selective C–H activation reactions with electron-rich compounds, since mild reagents can often been utilized in functional group metathesis reactions.