Rhodium(III)-catalyzed regioselective C2-alkenylation of indoles with CF3-imidoyl sulfoxonium ylides to give multi-functionalized enamines using a migratable directing group

Zuguang Yang; Jianhua Tang; Chen Li; Zhengkai Chen; Xiao-Feng Wu

doi:10.1039/d2cc06127a

Rhodium(III)-catalyzed regioselective C2-alkenylation of indoles with CF₃-imidoyl sulfoxonium ylides to give multi-functionalized enamines using a migratable directing group

Chem Commun (Camb). 2023 Jan 3;59(3):318-321. doi: 10.1039/d2cc06127a.

Authors

Zuguang Yang¹, Jianhua Tang¹, Chen Li¹, Zhengkai Chen¹, Xiao-Feng Wu^{2

3}

Affiliations

¹ Department of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, 310018, People's Republic of China. zkchen@zstu.edu.cn.
² Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, Liaoning, China. xwu2020@dicp.ac.cn.
³ Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straβe 29a, 18059, Rostock, Germany. xiao-feng.wu@catalysis.de.

PMID: 36511166
DOI: 10.1039/d2cc06127a

Abstract

A rhodium(III)-catalyzed regioselective C2-alkenylation of indoles for the construction of α-CF₃ substituted enamines has been developed, which utilizes CF₃-imidoyl sulfoxonium ylides (TFISYs) as alkenylating agents for the first time. A wide array of indolyl- and trifluoromethyl-decorated enamine derivatives have been assembled in moderate to good yields.