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Communication | Regular issue | Vol 104, No. 2, 2022, pp.267-274
Published online, 16th November, 2021
DOI: 10.3987/COM-21-14566
Heterogeneously Organocatalytic, Enantioselective Friedel-Crafts Alkylation of Indole with 3,3,3-Trifluoropyruvate

Pei Wang,* Jinhui Ni, Yong An, Xiaojiang Chen, Weiwei Zhang, Yang Zhang, and Guorong Ma

*School of Basic Medicine, Ningxia Medical University, Yinchuan, 750004, China

Abstract

The bifunctional tertiary amine-squaramide catalyst was synthesized with diphenylethylenediamine as the chiral framework and successfully catalyzed the asymmetric Friedel-Crafts alkylation reaction between indole and trifluoropyruvate. A series of trifluoromethylated indole derivatives were obtained with high yield (up to 95%) and moderate to good enantioselectivity (up to 76% ee). The reaction proceeds in heterogeneous system, the catalyst can be recovered by simple filtration and recycled.