Amide-directed Rhodium(III)-catalyzed C4—H Alkenylation of Indoles with gem-Difluoromethylene Alkynes

doi:10.1007/s40242-026-6029-9

Chemical Research in Chinese Universities ›› 2026, Vol. 42 ›› Issue (3): 971-982.doi: 10.1007/s40242-026-6029-9

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Amide-directed Rhodium(III)-catalyzed C4—H Alkenylation of Indoles with gem-Difluoromethylene Alkynes

DOU Chenyu¹, CAO Shi², LI Yahong¹, WANG Shouguo^2,3

1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P. R. China;
2. College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen, 518060, P. R. China;
3. Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen, 518055, P. R. China

Received:2026-01-24 Accepted:2026-02-27 Published:2026-06-02
Contact: LI Yahong,E-mail:liyahong@suda.edu.cn;WANG Shouguo,E-mail:shouguo.wang@szu.edu.cn E-mail:liyahong@suda.edu.cn;shouguo.wang@szu.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (No. 82350710800), the Guangdong Basic and Applied Basic Research Foundation, China (Nos. 2024A1515011368 and 2024QN11C213), the Shenzhen Science and Technology Program, China (No. KQTD20221101093605019), and the Scientific Foundation for Youth Scholars of Shenzhen University, China (No. 868-000001033009). WANG Shouguo is indebted to Shenzhen University for providing a starting grant.

Abstract

Abstract: The direct and selective C4—H functionalization of indoles remains a significant synthetic challenge. Addressing this, we disclose a highly efficient Rh(III)-catalyzed C4—H alkenylation of indoles employing gem-difluoromethylene alkynes. This directing group-assisted protocol delivers valuable difluorinated indole derivatives in excellent yields (up to 88%), with a broad substrate scope and exceptional functional group tolerance, providing a practical and versatile route for appealing indole diversification.

Key words: C—H activation, Indole, Rhodium catalysis, gem-Difluoromethylene alkyne

DOU Chenyu, CAO Shi, LI Yahong, WANG Shouguo. Amide-directed Rhodium(III)-catalyzed C4—H Alkenylation of Indoles with gem-Difluoromethylene Alkynes[J]. Chemical Research in Chinese Universities, 2026, 42(3): 971-982.

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Amide-directed Rhodium(III)-catalyzed C4—H Alkenylation of Indoles with gem-Difluoromethylene Alkynes

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