Journal
ORGANIC LETTERS
Volume 22, Issue 23, Pages 9342-9345Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03554
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Funding
- National Natural Science Foundation of China [21101085]
- Natural Science Foundation of Liaoning Province [2015020196]
- Liaoning Revitalization Talents Program [XLYC1902085]
- Research Fund of Key Laboratory of Synthetic Rubber-Changchun Institute of Applied Chemistry [KLSR1602]
- Doctoral Start-up Foundation of Liaoning Province [20180540085]
- Petro-China Innovation Foundation [2018D-5007-0507]
- Research Project Fund of the Liaoning Provincial Department of Education [L2019037]
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An efficient and mild Zn-mediated decarboxylative/defluorinative alkylation of alpha-trifluoromethyl alkenes using N-hydroxyphthahmide esters as radical precursors was developed. Several a-trifluoromethyl alkenes were readily coupled to a wide range of primary, secondary, and tertiary radicals, affording the desired gem-difluoroethylenes in moderate to excellent yields. This reaction protocol was also successfully applied to the construction of complex molecules such as the bioactive natural dehydroabietic acid and glycosyl groups bearing the gem-difluoroethylene moiety.
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