期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2020, 期 17, 页码 2600-2604出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000289
关键词
C-H alkylation; Heteroarenes; Cyclopropanol; beta-Heteroarylated ketones; Ring-opening
资金
- Science Foundation for Distinguished Scholars of Dongguan University of Technology [196100041, 196100041051]
- Postdoctor Foundation of Dongguan University of Technology [196100040006]
- National Natural Science Foundation of China [51773165, 51973171]
Direct C-H beta-carbonyl alkylation of heteroarenes under metal-, acid- and photo-catalyst free conditions has been achieved. A wide scope of substrates, such as various substituted quinolines and isoquinolines, pyridines, pyridazine, benzo[d]thiazole and phenanthroline, underwent the beta-carbonyl alkylation efficiently via K2S2O8-mediated ring-opening of cyclopropanols. The corresponding beta-heteroarylated ketones were obtained in moderate to excellent yields and gram-scale experiments further demonstrated the practicality of this synthetic protocol. The readily available reagents, mild and environmentally benign conditions make the method extremely attractive. The reaction mechanism is also proposed.
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