Formal C-H/C-I Metathesis: Site-Selective C-H Iodination of Anilines Using Aryl Iodides

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(sp(2))-H/C(sp(2))-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.

Automated summary

Functional group metathesis has the potential to provide mild reaction conditions for C-H functionalization. This study reports the meta- and ortho-C-H iodination of aniline derivatives using 2-nitrophenyl iodides as mild iodinating reagents. The results demonstrate the potential for developing novel site-selective C-H activation reactions with electron-rich compounds using mild reagents.