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Allylic C-H Activations Using Cu(II) 2-Quinoxalinol Salen and tert-Butyl Hydroperoxide

Yuancheng Li, Tae Bum Lee, Tanyu Wang, Audrey V. Gamble and Anne E. V. Gorden*

*Department of Chemistry and Biochemistry, College of Science and Mathematics, Auburn University, Auburn, Alabama 36849-5319, United States, Email: gordeaeauburn.edu

Y. Li, T. B. Lee, T. Tang, A. V. Gamble, A. E. V. Gorden, J. Org. Chem., 2012, 77, 4628-4633.

DOI: 10.1021/jo300372q (free Supporting Information)


Abstract

Olefin substrates can be converted to the corresponding enones or 1,4-enediones in very good yields in short reaction times using a Cu(II) 2-quinoxalinol salen complex as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant via allylic activation. The reaction tolerates many additional functional groups.

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Key Words

Allylic Oxidation, Cyclohexenones, tert-butyl hydroperoxide (TBHP)


ID: J42-Y2012-1450