Copper-Catalyzed Aerobic Decarboxylation/Ketooxygenation of Electron-Deficient Alkenes

Qingquan Lu; Pan Peng; Yi Luo; Ying Zhao; Minxian Zhou; Aiwen Lei

doi:10.1002/chem.201503716

Copper-Catalyzed Aerobic Decarboxylation/Ketooxygenation of Electron-Deficient Alkenes

Chemistry. 2015 Dec 14;21(51):18580-3. doi: 10.1002/chem.201503716. Epub 2015 Nov 6.

Authors

Qingquan Lu¹, Pan Peng¹, Yi Luo¹, Ying Zhao², Minxian Zhou², Aiwen Lei^{3

4}

Affiliations

¹ College of Chemistry and Molecular Sciences, the Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, Hubei (P. R. China).
² National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, Jiangxi (P. R. China).
³ College of Chemistry and Molecular Sciences, the Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, Hubei (P. R. China). aiwenlei@whu.edu.cn.
⁴ National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, Jiangxi (P. R. China). aiwenlei@whu.edu.cn.

PMID: 26486761
DOI: 10.1002/chem.201503716

Abstract

A copper-catalyzed ketooxygenation of electron-deficient alkenes was developed. This approach combines O-H alkylation, aerobic decarboxylation, and oxygenation in one transformation. Mechanistic investigation of this reaction showed that the copper salt is responsible for both generating the amidoxyl radical and promoting aerobic decarboxylation.

Keywords: copper catalysis; decarboxylation; dioxygen activation; oxidative coupling; radical coupling.

Publication types

Research Support, Non-U.S. Gov't