Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 14, Pages 7159-7164Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00619
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Funding
- National Natural Science Foundations of China [21372068, 21572049]
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A direct alpha-Csp(3)-H methylenation of arylke-tones 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 alpha,beta-unsatirated 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 alpha,beta-unsaturated carbonyl compounds. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.
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