Synthesis of Thioethers, Arenes and Arylated Benzoxazoles by Transformation of C(aryl)−C Bond of Aryl Alcohols

Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of C(aryl)−C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)−C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via cleavage of C(aryl)−C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohols conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)−C(OH) bonds in its linkages.