Direct Vinylation and Difluorovinylation of Arylboronic Acids Using Vinyl- and 2,2-Difluorovinyl Tosylates via the Suzuki−Miyaura Cross Coupling

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Abstract

General reaction conditions were developed for the Pd(0)-catalyzed Suzuki−Miyaura coupling reaction of aryl boronic acids with a simple electrophilic vinylation reagent, vinyl tosylate, providing access to styrene derivatives in good yields. The easily accessible vinyl tosylate represents a stable and less toxic alternative to the vinyl halides and the triflate/nonaflate derivatives. Furthermore, this methodology was expanded to provide a facile and straightforward approach for the introduction of a gem-difluorovinyl substituent onto an aromatic ring using the similar and also readily available 2,2-difluorovinyl tosylate as the electrophilic complement.

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

• 

  Monofluorovinyl Tosylate: A Useful Building Block for the Synthesis of Terminal Vinyl Monofluorides via Suzuki−Miyaura Coupling

  He Zhang, Chang-Bing Zhou, Qing-Yun Chen, Ji-Chang Xiao, and Ran Hong
  Organic Letters2011 13 (4), 560-563

  • Monofluorovinyl Tosylate: A Useful Building Block for the Synthesis of Terminal Vinyl Monofluorides via Suzuki−Miyaura Coupling

    He Zhang, Chang-Bing Zhou, Qing-Yun Chen, Ji-Chang Xiao, and Ran Hong
    Organic Letters2011 13 (4), 560-563

    Monofluorovinyl tosylate was developed as a practical vinyl fluoride building block to couple with a variety of arylboronic acids in the presence of a palladium catalyst. The high stereoselectivity of 2-aryl-1-fluoroethene derivatives was achieved. This ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  General, Robust, and Stereocomplementary Preparation of α,β-Disubstituted α,β-Unsaturated Esters

  Hidefumi Nakatsuji, Hiroshi Nishikado, Kanako Ueno and Yoo Tanabe
  Organic Letters2009 11 (19), 4258-4261

  • General, Robust, and Stereocomplementary Preparation of α,β-Disubstituted α,β-Unsaturated Esters

    Hidefumi Nakatsuji, Hiroshi Nishikado, Kanako Ueno and Yoo Tanabe
    Organic Letters2009 11 (19), 4258-4261

    An (E)- and (Z)-stereocomplementary preparative method for α,β-disubstituted α,β-unsaturated esters is performed via three general and robust reaction sequences: (i) Ti−Claisen condensation (formylation) of esters to give α-formyl esters (12 examples, ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Nickel-Catalyzed Vinylation of Aryl Chlorides and Bromides with Vinyl ZnBr·MgBrCl

  Tetsuya Yamamoto and Tetsu Yamakawa
  The Journal of Organic Chemistry2009 74 (9), 3603-3605

  • Nickel-Catalyzed Vinylation of Aryl Chlorides and Bromides with Vinyl ZnBr·MgBrCl

    Tetsuya Yamamoto and Tetsu Yamakawa
    The Journal of Organic Chemistry2009 74 (9), 3603-3605

    The Ni-catalyzed cross-coupling of aryl halides and vinylzinc bromide for the synthesis of styrene derivatives was investigated. Of the catalysts surveyed, the combination of Ni(acac)2 and Xantphos was found to be the most effective for this cross-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Direct Vinylation and Difluorovinylation of Arylboronic Acids Using Vinyl- and 2,2-Difluorovinyl Tosylates via the Suzuki−Miyaura Cross Coupling

  Thomas M. Gøgsig, Lina S. Søbjerg, Anders T. Lindhardt (neé Hansen), Kim L. Jensen and Troels Skrydstrup
  The Journal of Organic Chemistry2008 73 (9), 3404-3410

  • Direct Vinylation and Difluorovinylation of Arylboronic Acids Using Vinyl- and 2,2-Difluorovinyl Tosylates via the Suzuki−Miyaura Cross Coupling

    Thomas M. Gøgsig, Lina S. Søbjerg, Anders T. Lindhardt (neé Hansen), Kim L. Jensen and Troels Skrydstrup
    The Journal of Organic Chemistry2008 73 (9), 3404-3410

    General reaction conditions were developed for the Pd(0)-catalyzed Suzuki−Miyaura coupling reaction of aryl boronic acids with a simple electrophilic vinylation reagent, vinyl tosylate, providing access to styrene derivatives in good yields. The easily ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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