Copper-Catalyzed Protoarylation of gem-Difluoroallenes

A copper-catalyzed protoarylation of gem-difluoroallenes with aryl boronic esters has been developed, enabling highly regioselective synthesis of gem-difluoroalkenes in high yields. The mild reaction conditions allow for a variety of functional groups to be tolerated, and the reaction can be extende...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 2; pp. 525 - 529
Main Authors Li, Wei, Wang, Cheng, Xiao, Mengdie, Cheng, Li-Jie
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.01.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
FLUORINE
DESIGN
ACID
SULFONE
BIOLOGICAL-ACTIVITY
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Summary:A copper-catalyzed protoarylation of gem-difluoroallenes with aryl boronic esters has been developed, enabling highly regioselective synthesis of gem-difluoroalkenes in high yields. The mild reaction conditions allow for a variety of functional groups to be tolerated, and the reaction can be extended to protoalkenylation of gem-difluoroallenes. The synthetic utility of this method has been demonstrated in gram-scale operation as well as synthesis of chiral gem-difluoroalkenes bearing γ-carbon stereogenic centers in moderate enantioselectivity using a chiral bidentate phosphine ligand with a copper catalyst.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c03995