Deoxygenative ortho-Benzylation of Aryl Iodides with Benzyl Alcohol via Palladium/Norbornene Cooperative Catalysis

Abstract

Herein, we demonstrate a robust palladium/norbornene-catalyzed deoxygenative ortho-benzylation of aryl iodides with non-derivatized benzyl alcohol, enabling assembly of various diarylmethanes with high efficiency. Assisted by carbodiimides, alcohol was transiently converted into corresponding isoureas, which further polarize C-O bond, and facilitated the reaction with key ANP intermediate through nitrogen atom coordination. The salient features of this methodology include operational simplicity, high chemoselectivity, and broad substrate scope. Preliminary mechanistic investigation determined the higher reactivity of isourea over benzyl (pseudo)halide.