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I2-Catalyzed Direct α-Hydroxylation of β-Dicarbonyl Compounds with Atmospheric Oxygen under Photoirradiation

Chun-Bao Miao*, Yan-Hong Wang, Meng-Lei Xing, Xin-Wei Lu, Xiao-Qiang Sun* and Hai-Tao Yang

*School of Petrochemical Engineering, Changzhou University, Changzhou 213164, People’s Republic of China, Email: estallyyahoo.com, sunxiaoqiangyahoo.com

C.-B. Miao, Y.-H. Wang, M.-L. Xing, X.-W. Lu, X.-Q. Sun, H.-T. Yang, J. Org. Chem., 2013, 78, 11584-11589.

DOI: 10.1021/jo401866p (free Supporting Information)


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Abstract

An I2-catalyzed hydroxylation of β-dicarbonyl moieties using air as the oxidant under photoirradiation gives α-hydroxy-β-dicarbonyl compounds. With α-unsubstituted malonates, the hydroxylated dimerization product was afforded as the predominant product along with a minor product, α,α-dihydroxyl malonate.

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Key Words

α-hydroxylation, iodine, oxygen


ID: J42-Y2013