Pd-Catalyzed Transfer of Difluorocarbene

The study of transition-metal difluorocarbene complex has long been a subject of active investigation, but the transition-metal-catalyzed transfer of difluorocarbene remains a significant challenge. The Pd-catalyzed transfer of difluorocarbene is described to realize the coupling reaction of boronic...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 17; pp. 4384 - 4387
Main Authors Deng, Xiao-Yun, Lin, Jin-Hong, Xiao, Ji-Chang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
IODIDES
PHOSPHABETAINE
COPPER-MEDIATED DIFLUOROMETHYLATION
COMPLEXES
C-F BONDS
TETRAFLUOROETHYLENE
DIAZO-COMPOUNDS
ARYL
METATHESIS
TRIFLUOROMETHYLATION
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Summary:The study of transition-metal difluorocarbene complex has long been a subject of active investigation, but the transition-metal-catalyzed transfer of difluorocarbene remains a significant challenge. The Pd-catalyzed transfer of difluorocarbene is described to realize the coupling reaction of boronic acids with difluorocarbene to give (difluoromethyl)­arenes and -olefins. Mechanistic investigations reveal that the PdCF2 complex is an important intermediate for this transformation. This complex is prone to trimerization without the presence of starting materials.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b02141