Copper-Catalyzed Protoarylation of -Difluoroallenes.

Org Lett

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, People's Republic of China.

Published: January 2024

A copper-catalyzed protoarylation of -difluoroallenes with aryl boronic esters has been developed, enabling highly regioselective synthesis of -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 -difluoroallenes. The synthetic utility of this method has been demonstrated in gram-scale operation as well as synthesis of chiral -difluoroalkenes bearing γ-carbon stereogenic centers in moderate enantioselectivity using a chiral bidentate phosphine ligand with a copper catalyst.

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http://dx.doi.org/10.1021/acs.orglett.3c03995DOI Listing

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Copper-Catalyzed Protoarylation of -Difluoroallenes.

Org Lett

January 2024

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, People's Republic of China.

A copper-catalyzed protoarylation of -difluoroallenes with aryl boronic esters has been developed, enabling highly regioselective synthesis of -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 -difluoroallenes. The synthetic utility of this method has been demonstrated in gram-scale operation as well as synthesis of chiral -difluoroalkenes bearing γ-carbon stereogenic centers in moderate enantioselectivity using a chiral bidentate phosphine ligand with a copper catalyst.

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