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Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air

Hai-Jun Zhang, Alexander W. Schuppe, Shi-Tao Pan, Jin-Xiang Chen, Bo-Ran Wang, Timothy R. Newhouse* and Liang Yin*

*Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States; Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032, China, Email: timothy.newhouseyale.edu, liangyinsioc.ac.cn

H.-J. Zhang, A. W. Schuppe, S.-T. Pan, J.-X. Chen, B.-R. Wang, T. R. Newhouse, L. Yin, J. Am. Chem. Soc., 2018, 140, 5300-5310.

DOI: 10.1021/jacs.8b01886 (free Supporting Information)


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Abstract

A mild and operationally simple copper-catalyzed vinylogous aerobic oxidation of β,γ- and α,β-unsaturated esters features good yields, broad substrate scope, excellent chemo- and regioselectivity, and good functional group tolerance. This method is additionally capable of oxidizing β,γ- and α,β-unsaturated aldehydes, ketones, amides, nitriles, and sulfones.

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Key Words

allylic alcohols, air


ID: J48-Y2018