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Iridium-Catalyzed Aerobic α,β-Dehydrogenation of γ,δ-Unsaturated Amides and Acids: Activation of Both α- and β-C-H bonds through an Allyl-Iridium Intermediate

Zhen Wang, Zhiqi He, Linrui Zhang and Yong Huang*

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

Z. Whang, Z. He, L. Zhang, Y. Huang, J. Am. Chem. Soc., 2018, 140, 735-740.

DOI: 10.1021/jacs.7b11351 (free Supporting Information)


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Abstract

A simple iridium/copper relay catalysis system enables a direct aerobic α,β-dehydrogenation of γ,δ-unsaturated amides and carboxylic acids to provide conjugated dienamides and dienoic acids in excellent yield. Instead of α-C-H metalation, this reaction proceeds by β-C-H activation, which results in enhanced α-acidity.


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Key Words

α,β-unsaturated carboxylic acid derivatives, 1,3-dienes, oxygen


ID: J48-Y2018