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Palladium-Catalyzed Oxidative Rearrangement of Tertiary Allylic Alcohols to Enones with Oxygen in Aqueous Solvent

Jingjie Li, Ceheng Tan, Jianxian Gong* and Zhen Yang*

*Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China, Email: gongjxpku.edu.cn, zyangpku.edu.cn

J. Li, C. Tan, J. Gong, Z. Yang, Org. Lett., 2014, 16, 5370-5373.

DOI: 10.1021/ol502578h (free Supporting Information)


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Abstract

A Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols gives secondary allylic alcohols. In a one-pot procedure, a subsequent Pd(TFA)2/neocuproine-catalyzed oxidation leads to β-disubstituted-α,β-unsaturated enones directly.

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Key Words

allylic alcohols


ID: J54-Y2014