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

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 sta...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-10, Vol.2019 (37), p.6417-6421
Main Authors: Blahun, Oleksandr P., Redka, Mykhailo O., Voitenko, Zoia V., Kysil, Andrii I., Dobrydnev, Alexey V., Grygorenko, Oleksandr O.
Format: Article
Language:English
Subjects:
Aromatic compounds
Bromides
C–C coupling
Fluorination
Functional groups
Homogeneous catalysis
Organoboron compounds
Organofluorine compounds
Reagents
Substrates
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Summary: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 °C for months. The Pd(dppf)Cl2‐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. Multigram preparation and Suzuki–Miyaura reactions of a novel fluorinated reagent for the synthesis of gem‐difluorostyrenes, their heterocyclic analogues, as well as gem‐difluorodienes – 2,2‐difluorovinyl pinacolborane – is described.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901118