Synthesis of 2-(2-Nitroalkyl)indoles by Rhodium(III)-Catalyzed C–H Alkylation

• DOI: 10.1021/acs.orglett.3c00057
• Publication Date: 2023-02-28T21:18:33Z
• Authors: Shuang-Liang Liu; Ru Zhao; Menglong Li; Haoran Yang; Liming Zhou; Shaoming Fang
• Keywords: Pyrrole; Friedel–Crafts reaction

The Rh(III)-catalyzed addition of the indole C2–H bond to nitroalkenes under an ambient atmosphere is disclosed, providing direct access a wide range 2-(2-nitroalkyl)indoles (33 examples) with excellent chemo- and regioselectivity. In addition, pyrrole derivatives also successfully participated in this Friedel–Crafts alkylation reaction. Representative nitroalkane products could be converted into structurally diverse valuable derivatives. Furthermore, series control experiments were conducted, plausible mechanism was proposed.