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

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posted on 03.04.2015 by Kun Guo, Xiaolan Chen, Mingyu Guan, Yingsheng Zhao
A simple and practical exo-oxime ether auxilixary for ortho-C–H functionalization of aromatic alcohols has been developed. Selective olefination of aromatic alcohols were first achieved via a six- or seven-membered exo-acetone oxime ether palladacycle with broad substrate scope. In addition, the crystal of the exo-palladacycle intermediate was obtained for the first time, and the application of this method in total synthesis of 3-deoxyisoochracinic acid was accomplished via a novel retro-synthetic disconnection approach, thus demonstrating the utility of this transformation.