Synthesis of 2-(2-Nitroalkyl)indoles by Rhodium(III)-Catalyzed C–H Alkylation
Shuang‐Liang Liu, Zhao Ru, Menglong Li, Haoran Yang, Liming Zhou, Shao‐Ming Fang
Abstract
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.
Topics & Concepts
ChemistryAlkylationIndole testRegioselectivityRhodiumPyrroleCatalysisMedicinal chemistryOrganic chemistryCombinatorial chemistryFriedel–Crafts reactionCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis