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Wacker-Type Oxidation and Dehydrogenation of Terminal Olefins Using Molecular Oxygen as the Sole Oxidant without Adding Ligand

Yu-Fei Wang, Ya-Ru Gao, Shuai Mao, Yan-Lei Zhang, Dong-Dong Guo, Zhao-Lei Yan, Shi-Huan Guo and Yong-Qiang Wang*

*Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. China, Email: wangyqnwu.edu.cn

Y.-F. Wang, Y.-R. Gao, S. Mao, Y.-L. Zhang, D.-D. Guo, Z.-L. Yan, S.-H. Guo, Y.-Q. Wang, Org. Lett., 2014, 16, 1610-1613.

DOI: 10.1021/ol500218p (free Supporting Information)


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Abstract

An efficient and economical ligand-free palladium-based oxidation system using molecular oxygen as the sole oxidant enables the Tsuji-Wacker oxidation of terminal olefins and especially styrenes to methyl ketones. In addition, this system achieves a tandem Wacker oxidation-dehydrogenation sequence of terminal olefins to yield α,β-unsaturated ketones.

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Key Words

Wacker-Tsuji Oxidation, Enones, Oxygen


ID: J54-Y2014