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

ABSTRACT

A discovery that the inexpensive Br₂ can serve as a potent Lewis acid catalyst for bis(2-hydroxy-1-naphthyl)methanes synthesis is presented. Under the catalysis of Br₂ 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 Br₂ is a potent Lewis acid to activate the carbonyl group, yet it was not the primary cause for the remarkable activity of Br₂ in the current communication.

GRAPHICAL ABSTRACT

KEYWORDS:

• Alkylation
• bromine effect
• C–C coupling
• homogeneous catalysis