One-pot, three-component regioselective coupling reaction of triphenylamine/carbazole derivatives with [60]fullerene and indoles via an “umpolung relay” strategy

Xin-Rui Chen; Qian-Wen Zhang; Ge-Ge Tao; Jun Xuan; Hong-Ping Zhou; Yu-Peng Tian; Fei Li

doi:10.1039/D1QO01058A

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One-pot, three-component regioselective coupling reaction of triphenylamine/carbazole derivatives with [60]fullerene and indoles via an “umpolung relay” strategy†

Xin-Rui Chen,^a Qian-Wen Zhang,^a Ge-Ge Tao,^a Jun Xuan,

^a Hong-Ping Zhou,

^a Yu-Peng Tian

^a and Fei Li

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Anhui University; Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University), Ministry of Education; Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province, Hefei, Anhui 230601, China
E-mail: lfe@ahu.edu.cn

Abstract

An efficient “umpolung relay” three-component regioselective coupling reaction of triphenylamine/carbazole derivatives with C₆₀ and indoles was developed. This new methodology includes a one-pot, double polarity inversion of C₆₀, and thus achieved a cascade reaction of aromatic (indole) nucleophilic addition and electrophilic substitution of arenes (triphenylamine/carbazole). This protocol features high regioselectivity, broad substrate scope, and excellent functional group tolerance that includes bromo, ester, nitro, cyano, formyl, and N–H groups on the arenes.

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Correction: One-pot, three-component regioselective coupling reaction of triphen…

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DOI: https://doi.org/10.1039/D1QO01058A
Article type: Research Article
Submitted: 18 Jul 2021
Accepted: 31 Aug 2021
First published: 31 Aug 2021

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Org. Chem. Front., 2021,8, 5994-5999

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One-pot, three-component regioselective coupling reaction of triphenylamine/carbazole derivatives with [60]fullerene and indoles via an “umpolung relay” strategy

X. Chen, Q. Zhang, G. Tao, J. Xuan, H. Zhou, Y. Tian and F. Li, Org. Chem. Front., 2021, 8, 5994 DOI: 10.1039/D1QO01058A

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Organic Chemistry Frontiers

One-pot, three-component regioselective coupling reaction of triphenylamine/carbazole derivatives with [60]fullerene and indoles via an “umpolung relay” strategy†

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Supplementary files

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One-pot, three-component regioselective coupling reaction of triphenylamine/carbazole derivatives with [60]fullerene and indoles via an “umpolung relay” strategy

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