Stereoselective Synthesis of Difluorinated 1,3-Dienes via Palladium-Catalyzed C-F Bond Activation of Tetrasubstituted gem-Difluoroalkenes

被引：14

作者：

Wang, Yanhui ^{[1
]}

Ma, Qiao ^{[1
]}

Tsui, Gavin Chit ^{[1
]}

机构：

[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 13期

关键词：

CROSS-COUPLING REACTIONS; ARYL HALIDES; BORYLATION; HYDRODEFLUORINATION; DEFLUOROBORYLATION; ROUTE;

D O I：

10.1021/acs.orglett.1c01768

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly diastereoselective Pd(0)-catalyzed synthesis of difluorinated 1,3-dienes is described. Symmetrical 1,3-dienes containing a vicinal difluoro moiety can be obtained as single diastereomers from tetrasubstituted gem-difluoroalkenes. The reaction presumably proceeds through a stereoselective twofold Pd-catalyzed Miyaura borylation/Suzuki-Miyaura cross-coupling of the C-F bond. Moreover, modular synthesis of unsymmetrical difluorinated 1,3-dienes is also achievable by the coupling between gem-difluoroalkenes and borylated monofluoroalkenes.

引用

页码：5241 / 5245

页数：5

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