Direct ortho-C-H functionalization of aromatic alcohols masked by acetone oxime ether via exo-palladacycle

Organic Letters
Kun GuoYingsheng Zhao

Abstract

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.

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Citations

Apr 11, 2017·Journal of the American Chemical Society·Veronika M Shoba, James M Takacs
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Aug 18, 2018·Organic & Biomolecular Chemistry·Ling-Yan ShaoYa-Fei Ji
Jul 24, 2018·Angewandte Chemie·Yuanyuan HuCongyang Wang
Sep 5, 2019·Angewandte Chemie·Conghui TangDavid Sarlah

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