Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Transition Metal-Free α-Csp3-H Methylenation of Ketones to Form CC Bond Using Dimethyl Sulfoxide as Carbon Source
Yu-Qun Hu, Peng-Yi Ji, Qiang Liu, Yu-Feng Liu, Can-Cheng Guo, Jing-Wen Xu, Wei-Ping Luo
A direct α-Csp3-H methylenation of arylketones to form C═C bond using dimethyl sulfoxide as one-carbon source is achieved under transition metal-free reaction condition. Various aryl ketone derivatives react readily with DMSO, producing the α,β-unsaturated carbonyl compounds in yields of 42 to 90%. This method features a transition metal-free reaction condition, wide substrate scope and using DMSO as novel one-carbon source to form C═C bond, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyl compounds. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00619

DOI: 10.1021/acs.joc.7b00619

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