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One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts

Weijie Ding, Juan Hu, Huile Jin, Xiaochun Yu*, Shun Wang*

*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China, Email: xiaochunyuwzu.edu.cn, shunwangwzu.edu.cn

W. Ding, J. Hu, H. Jin, X. Yu, S. Wang, Synthesis, 2018, 50, 107-118.

DOI: 10.1055/s-0036-1590904 (free Supporting Information)


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Abstract

The combination of a copper-catalyzed oxidation in the presence of oxygen, a deprotonation, and a Wittig reaction enables the synthesis of α,β-unsaturated esters, ketones, and nitriles from alcohols and functionalized phosphonium salts. The solvent mixture of acetonitrile and formamide (1:1) is optimized for all part reactions.

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Key Words

oxidation of alcohols, oxygen, phosphonium salts, tandem reaction, copper catalyst, Wittig reaction, carbon-carbon double bonds, enones


ID: J66-Y2018