☆ 4.8 Article

Copper-Catalyzed Oxidative Cleavage of Electron-Rich Olefins in Water at Room Temperature

ORGANIC LETTERS (2018)

Journal

ORGANIC LETTERS

Volume 20, Issue 17, Pages 5094-5097

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.8b01883

Keywords

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Categories

Chemistry, Organic

Funding

Novartis
NSF [SusChEM 1561158]
CONACyT [409406, 258048]
Posgrado en Ciencias Quimicas

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Abstract

A copper-catalyzed oxidative cleavage of electron-rich olefins into their corresponding carbonyl derivatives is described as an alternative to ozonolysis. The scope includes various precursors to aryl ketone derivatives, as well as oxidations of enol ethers bearing atypical alkyl and dialkyl substitution, the first of their kind among such metal catalyzed alkene cleavage reactions. The use of an inexpensive copper salt, room temperature conditions, an aerobic atmosphere, and water as the global reaction medium highlight the green features of this new method. Associated mechanistic investigations are also presented.

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