Dearomatization-Rearomatization Strategy for ortho-Selective Alkylation of Phenols with Primary Alcohols

Phenols are common precursors and core structures of a variety of industrial chemicals ranging from pharmaceuticals to polymers. However, the synthesis of site-specifically substituted phenols is challenging, and thus the development of new methods for this purpose would be highly desirable. Reported here is a protocol for palladium-catalyzed ortho-selective alkylation reactions of phenols with primary alcohols by a dearomatization-rearomatization strategy, with water as the sole by-product. Various substituted phenols and primary alcohols were compatible with the standard reaction conditions. The detailed mechanism of this transformation was also investigated.

Automated summary

This study presents a new method for palladium-catalyzed alkylation reactions of phenols with primary alcohols, using a dearomatization-rearomatization strategy with water as the only by-product. Various substituted phenols and primary alcohols are compatible with the standard reaction conditions.