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Metal-Free, NHPI Catalyzed Oxidative Cleavage of C-C Double Bond Using Molecular Oxygen as Oxidant

Riyuan Lin, Feng Chen and Ning Jiao*

*State Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China, Email:

R. Lin, F. Chen, N. Jiao, Org. Lett., 2012, 14, 4158-4161.

DOI: 10.1021/ol3018215


N-hydroxyphthalimide (NHPI) catalyzes a metal-free, aerobic oxidative cleavage of olefins. This methodology avoids the use of toxic metals or overstoichiometric amounts of traditional oxidants, showing good economical and environmental advantages. Based on the experimental observations, a plausible mechanism is proposed.

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Key Words

Cleavage of Alkenes, Oxygen, Green Chemistry, Organocatalysis

ID: J54-Y2012-2540