Direct ortho-C–H Functionalizationof Aromatic Alcohols Masked by Acetone Oxime Ether via exo-Palladacycle.

A simple and practical exo-oxime ether auxilixaryfor ortho-C–H functionalization of aromaticalcohols has been developed. Selective olefination of aromatic alcoholswere first achieved via a six- or seven-membered exo-acetone oxime ether palladacycle with broad substrate scope. Inaddition, the crystal of the exo-palladacycle intermediatewas obtained for the first time, and the application of this methodin total synthesis of 3-deoxyisoochracinic acid was accomplished viaa novel retro-synthetic disconnection approach, thus demonstratingthe utility of this transformation. [ABSTRACT FROM AUTHOR]