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Fe-Catalyzed Aerobic Oxidative C-CN Bond Cleavage of Arylacetonitriles Leading to Various Esters

Weiguang Kong, Bingnan Li, Xuezhao Xu and Qiuling Song*

*Institute of Next Generation Matter Transformation, College of Chemical Engineering, College of Materials Science & Engineering, Huaqiao University, 668 Jimei Blvd, Xiamen, Fujian 361021, P. R. China, Email: qsonghqu.edu.cn

W. Kong, B. Li, X. Xu, Q. Song, J. Org. Chem., 2016, 81, 8436-8443.

DOI: 10.1021/acs.joc.6b01594 (free Supporting Information)



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Abstract

In a Fe-catalyzed aerobic oxidative esterifications of arylacetonitriles, acyl electrophiles were in situ generated via chemoselective C(CO)-CN bond cleavage. Alcohols, alkoxsilanes, silicate esters, or borate esters can be acylated to the corresponding aryl esters in good to excellent yields under molecular oxygen. Dioxygen serves as both oxidant and reactant.

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Key Words

oxidation, esters, oxygen


ID: J42-Y2016