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Catalyst-Controlled Chemodivergent Modification of Indoles with 2-Furylcarbinols: Piancatelli Reaction vs Cross-Dehydrative Coupling Reaction

descriptionPublicationkeyboard_double_arrow_right Article , Journal 09 Mar 2017Publisher:American Chemical Society (ACS)Journal:The Journal of Organic Chemistry, volume 82, pages 3,561-3,570 (issn: 0022-3263, eissn: 1520-6904,

Authors: Jianfeng Xu; Yi Luo; Huaping Xu; Zhengkai Chen; Maozhong Miao; Hongjun Ren;

doi: 10.1021/acs.joc.7b00090

pmid: 28244319

Catalyst-Controlled Chemodivergent Modification of Indoles with 2-Furylcarbinols: Piancatelli Reaction vs Cross-Dehydrative Coupling Reaction

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Abstract

A divergent synthetic strategy to functionalize the indole nucleus with readily available 2-furylcarbinols was developed. It was found that the 3-(4-oxo-2-cyclopentenyl)indoles were obtained in moderate to good yields (up to 89%) through Piancatelli reaction catalyzed by ZnCl2, whereas employment of Brønsted acid TFA afforded directly coupled product 3-(2-furyl)indoles in moderate to good yields (up to 87%) via the deprotonation-rearomatization route.

Related Organizations

Zhejiang Sci-Tech University
China (People's Republic of)
Zhejiang Sci-Tech University
China (People's Republic of)

12 Research products, page 1 of 2

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