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

• DOI: 10.1021/acs.joc.7b00090
• Publication Date: 2017-02-28T10:40:28Z
• Authors: Jianfeng Xu; Yi Luo; Huaping Xu; Zhengkai Chen; Maozhong Miao; Hongjun Ren
• Keywords: 01 natural sciences; 0104 chemical sciences

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.