Transition Metal-Free α‑Csp3‑H Methylenation of Ketones to Form CC Bond Using Dimethyl Sulfoxide as Carbon Source
A direct α-Csp3-H methylenation of arylketones to form CC 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 in | Journal of organic chemistry Vol. 82; no. 14; pp. 7159 - 7164 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
American Chemical Society
21.07.2017
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Online Access | Get full text |
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Summary: | A direct α-Csp3-H methylenation of arylketones to form CC 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 CC 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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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.7b00619 |