期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 19, 页码 6357-6361出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902001
关键词
alkynes; boranes; lactones; radical reactions; synthetic methods
资金
- JSPS KAKENHI [16K08159]
- US National Science Foundation [CHE-1660927]
- Grants-in-Aid for Scientific Research [16K08159] Funding Source: KAKEN
Substituted propargyl acetates are converted into 4-boryl-2(5H)-furanones upon thermolysis in the presence of an N-heterocyclic carbene borane (NHC-borane) and di-tert-butyl peroxide. The acetyl methyl group is lost during the reaction as methane. Evidence suggests that the reaction proceeds by a sequence of radical events including: 1)addition of an NHC-boryl radical to the triple bond; 2)cyclization of the resultant -borylalkenyl radical to the ester carbonyl group; 3)-scission of the so-formed alkoxy radical to provide the 4-boryl-2(5H)-furanone and a methyl radical; and 4)hydrogen abstraction from the NHC-borane to return the initial NHC-boryl radical and methane.
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