Abstract
In this study, we reported a solvent-controlled site-selectivity switchable Friedel-Crafts reaction of 1-naphthols with in situ generated aza-o-quinone methides. The ortho-selective Friedel-Crafts reaction was achieved in toluene, while the para-selective Friedel-Crafts reaction was accomplished in acetonitrile. With this protocol, a range of functionalized triarylmethanes were prepared. Moreover, theoretical mechanistic investigations provided insights into the site-selective reaction pathway.