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
收藏
页码：5241 / 5245
页数：5
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