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

Org Lett

College of Material and Chemical Engineering and Key Laboratory of Surface and Interface Science and Technology of Henan Province, Zhengzhou University of Light Industry, Kexue Avenue 136, Zhengzhou 450001, People's Republic of China.

Published: March 2023

The Rh(III)-catalyzed addition of the indole C2-H bond to nitroalkenes under an ambient atmosphere is disclosed, providing direct access to a wide range of 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 and valuable indole derivatives. Furthermore, a series of control experiments were conducted, and a plausible mechanism was proposed.

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http://dx.doi.org/10.1021/acs.orglett.3c00057DOI Listing

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