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Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols

Xiaomin Xie and Shannon S. Stahl*

*Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States, Email: stahlchem.wisc.edu

X. Xie, S. S. Stahl, J. Am. Chem. Soc., 2015, 137, 3767-3770.

DOI: 10.1021/jacs.5b01036 (free Supporting Information)


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Abstract

Cu/nitroxyl catalysts promote a highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. A Cu/ABNO catalyst system shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols.

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Key Words

lactones, oxidative esterification, ABNO, TEMPO, oxygen


ID: J48-Y2015