Synthesis of gem-Difluoroalkenes via Zn-Mediated Decarboxylative/Defluorinative Cross-Coupling

An efficient and mild Zn-mediated decarboxylative/defluorinative alkylation of α-trifluoromethyl alkenes using N-hydroxyphthalimide esters as radical precursors was developed. Several α-trifluoromethyl alkenes were readily coupled to a wide range of primary, secondary, and tertiary radicals, affordi...

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Published inOrganic letters Vol. 22; no. 23; pp. 9342 - 9345
Main Authors Du, Hai-Wu, Chen, Yang, Sun, Jing, Gao, Qi-Sheng, Wang, He, Zhou, Ming-Dong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.12.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENES
DEFLUORINATIVE ALKYLATION
BIOLOGICAL-ACTIVITY
MONOFLUOROALKENES
PROGRESS
ESTERS
FLUORINE
C-F
F BOND ACTIVATION
CARBOXYLIC-ACIDS
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Summary:An efficient and mild Zn-mediated decarboxylative/defluorinative alkylation of α-trifluoromethyl alkenes using N-hydroxyphthalimide esters as radical precursors was developed. Several α-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.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03554