Transition Metal-Free α-Csp³-H Methylenation of Ketones to Form C═C Bond Using Dimethyl Sulfoxide as Carbon Source

Yu-Feng Liu, Peng-Yi Ji, Jing-Wen Xu, Yu-Qun Hu, Qiang Liu, Wei-Ping Luo and Can-Cheng Guo*

*College of Chemistry and Chemical Engineering, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha 410082, China, Email: ccguohnu.edu.cn

Y.-F. Liu, P. Yi Ji, J.-W. Xu, Y.-Q. Hu, Q. Liu, W.-P. Luo, C.-C. Guo, J. Org. Chem., 2017, 82, 7161-7164.

DOI: 10.1021/acs.joc.7b00619

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Abstract

Various aryl ketone derivatives react readily with DMSO under transition metal-free reaction condition, producing the α,β-unsaturated carbonyl compounds in good yields. This direct α-Csp³-H methylenation offers wide substrate scope and provides an efficient and expeditious approach to an important class of α,β-unsaturated carbonyl compounds.

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proposed mechanism

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Key Words

enones, terminal alkenes, potassium peroxydisulfate

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ID: J42-Y2017