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Rhodium(III)‐Catalyzed Direct C7‐Selective Alkenylation and Alkylation of Indoles with Maleimides

Yaoguang Sheng, Yi Gao, Bingbing Duan, Mengxia Lv, Yao Chen, Mengjie Yang, Jianmin Zhou, Guang Liang, Zengqiang Song

2021Advanced Synthesis & Catalysis23 citationsDOI

Abstract

Abstract A versatile and efficient method for the coupling of maleimides and indoles at the C7‐position has been established under Rh(III) catalysis. The present protocol was compatible with various functional groups, diverse 3‐(indol‐7‐yl)maleimides and 3‐(indol‐7‐yl)succinimides were obtained in moderate to excellent yields by switching reaction conditions. Moreover, this method further highlights the unique practical application for the conjugation with pharmaceutically useful compounds and amino acid derivatives. To explore the mechanism of this transformation, deuteration studies and control experiments have been carried out. magnified image

Topics & Concepts

ChemistrySuccinimidesRhodiumAlkylationCatalysisCombinatorial chemistryReaction conditionsOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis
Rhodium(III)‐Catalyzed Direct C7‐Selective Alkenylation and Alkylation of Indoles with Maleimides | Litcius