Synthesis
DOI: 10.1055/s-0036-1590904
paper
© Georg Thieme Verlag Stuttgart · New York

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*
Financial support from the National Natural Science Foundation of China (No. 21302143 and 51572198) and Natural Science Foundation of Zhejiang Province (No. LY13B020006 and LZ17E020002) is greatly appreciated.
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Publication History

Received: 17 July 2017

Accepted after revision: 10 August 2017

Publication Date:
12 September 2017 (eFirst)

Abstract

A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO2Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.

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