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

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%....

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Published inJournal of organic chemistry Vol. 82; no. 14; pp. 7159 - 7164
Main Authors Liu, Yu-Feng, Ji, Peng-Yi, Xu, Jing-Wen, Hu, Yu-Qun, Liu, Qiang, Luo, Wei-Ping, Guo, Can-Cheng
Format Journal Article
LanguageEnglish
Published American Chemical Society 21.07.2017
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Summary: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.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00619