Novel and potent Lewis acid catalyst: Br2-catalyzed Friedel-Crafts reactions of naphthols with aldehydes

作者:Liang, Deqiang*; Li, Jingjing; Li, Yanni*; Wang, Baoling; Cheng, Ping; Luo, Sha
来源:Synthetic Communications, 2016, 46(4): 379-385.
DOI:10.1080/00397911.2016.1139723

摘要

A discovery that the inexpensive Br-2 can serve as a potent Lewis acid catalyst for bis(2-hydroxy-1-naphthyl)methanes synthesis is presented. Under the catalysis of Br-2 at room temperature, naphthols reacted smoothly with various aldehydes with high efficiency and broad substrate scope. This reaction used to require highly acidic conditions and/or high temperature and/or pressure, and sometimes featured poor yields. Moreover, theoretical calculations suggested that Br-2 is a potent Lewis acid to activate the carbonyl group, yet it was not the primary cause for the remarkable activity of Br-2 in the current communication.