Journal
ORGANIC LETTERS
Volume 22, Issue 6, Pages 2419-2424Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00622
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Funding
- Natural Science Foundation of China [21572118, 21971149]
- Tang Scholar Award
- Fundamental Research Funds of Shandong Univ.
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A kinetically controlled radical addition/elimination reaction generating fluorinated allenes was developed. This strategy offers a route to a facile synthesis of diverse trifluoromethyl, difluoromethylene, and perfluoroalkyl functionalized allenes from readily available fluoroalkyl halides and alkynyl aziridines under visible-light irradiation. Density functional theory calculation of this radical clock type of reaction revealed a kinetically controlled C-N bond cleavage overcoming the alternative thermodynamically controlled C-C bond cleavage process.
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