2,2-Difluorovinyl Pinacolborane - A New Versatile Reagent for the Suzuki-Miyaura Reaction

被引：7

作者：

Blahun, Oleksandr P. ^{[1
,2
]}

Redka, Mykhailo O. ^{[1
,2
]}

Voitenko, Zoia V. ^{[2
]}

Kysil, Andrii I. ^{[2
]}

Dobrydnev, Alexey V. ^{[1
,2
]}

Grygorenko, Oleksandr O. ^{[1
,2
]}

机构：

[1] Enamine Ltd, Chervonotkatska St 78, UA-02094 Kiev, Ukraine

[2] Taras Shevchenko Natl Univ Kyiv, Volodymyrska St 60, UA-01601 Kiev, Ukraine

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 37期

关键词：

Organofluorine compounds; Organoboron compounds; C-C coupling; Homogeneous catalysis; CROSS-COUPLING REACTIONS; GEM-DIFLUOROALKENES; NUCLEOPHILIC DIFLUOROMETHYLATION; POTENTIAL INHIBITORS; CARBONYL-COMPOUNDS; CYCLIZATION; ROUTE; 1,1-DIFLUORO-1-ALKENES; DIFLUOROOLEFINATION; DIFLUOROVINYLATION;

D O I：

10.1002/ejoc.201901118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel fluorinated reagent for the synthesis of gem-difluorostyrenes and their heterocyclic analogues - 2,2-difluorovinyl pinacolborane (CF2=CHBPin) was developed. In particular, borylation of 1,1-difluoroethylene with isopropoxy pinacolborane afforded the title compound on a multigram scale as stable, easy-to-handle liquid which can be stored at +4 degrees C for months. The Pd(dppf)Cl-2-catalyzed cross-coupling of this reagent with (het)aryl and vinyl bromides works well with broad spectrum of substrates and is characterized by good yields, functional group tolerance, sufficient reproducibility, as well as scalability.

引用

页码：6417 / 6421

页数：5

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