meta-Selective O-Arylation of Cyclic Diaryliodonium Salts with Phenols via Aryne Intermediates

Herein, we report a base-mediated, highly meta-selective O-arylation process of phenols and cyclic diaryliodonium salts without usage of transition metals. This novel and practical method was proved to be useful for the synthesis of iodine-containing meta-functionalized biaryl ethers in a broad functional group tolerance and environmentally friendly manner. Diversity-oriented transformations of the products were carried out to give various valuable functionalized biaryls. Preliminary mechanistic studies support the proposed aryne generation mechanism.