This work describes a metal-free synthetic approach for arylation of phenols and alkanols with aryl iodidesvia the intermediacy of unsymmetrical diaryliodonium salts. Specifically, the aryl iodide is oxidized and trimethoxybenzene installed as a “dummy” aryl ligand on the iodine(III) leaving group on the aryl electrophile. The modification of the leaving and C-O coupling occur in a single pot streamlining the synthesis and facilitating novel chemoselectivity and providing access highly substituted ethers.

C-O coupling mediated by iodine(III) via in situ formation of diaryliodonium salts

ACS Fall 2021

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