Efficient Carbonylation Reactions in Phosphonium Salt Ionic Liquids:  Anionic Effects

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Abstract

Application of phosphonium salt ionic liquids in the carbonylation of aryl and vinyl halides is presented. Anionic effects were uncovered with the bromide ionic liquid emerging as the superior media. Acid bromide intermediates were detected in control experiments providing an extended view on the overall catalytic cycle involved. Solvent-free product isolation and recycling of the ionic liquid containing active Pd-catalyst are also demonstrated.

Citing Articles

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This article has been cited by 9 ACS Journal articles (5 most recent appear below).

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  Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2

  Jason P. Hallett and Tom Welton
  Chemical Reviews2011 111 (5), 3508-3576

  • Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2

    Jason P. Hallett and Tom Welton
    Chemical Reviews2011 111 (5), 3508-3576
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Development of a General Palladium-Catalyzed Carbonylative Heck Reaction of Aryl Halides

  Xiao-Feng Wu, Helfried Neumann, Anke Spannenberg, Thomas Schulz, Haijun Jiao, and Matthias Beller
  Journal of the American Chemical Society2010 132 (41), 14596-14602

  • Development of a General Palladium-Catalyzed Carbonylative Heck Reaction of Aryl Halides

    Xiao-Feng Wu, Helfried Neumann, Anke Spannenberg, Thomas Schulz, Haijun Jiao, and Matthias Beller
    Journal of the American Chemical Society2010 132 (41), 14596-14602

    The first general palladium-catalyzed carbonylative vinylation of aryl halides with olefins in the presence of CO has been developed. Applying a catalyst system consisting of [(cinnamyl)PdCl]2 and bulky imidazolyl-phosphine ligand L1 allows for the ...

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

  Palladium-Catalyzed Double Carbonylation Reactions of o-Dihaloarenes with Amines in Phosphonium Salt Ionic Liquids

  Hong Cao and Howard Alper
  Organic Letters2010 12 (18), 4126-4129

  • Palladium-Catalyzed Double Carbonylation Reactions of o-Dihaloarenes with Amines in Phosphonium Salt Ionic Liquids

    Hong Cao and Howard Alper
    Organic Letters2010 12 (18), 4126-4129

    Palladium-catalyzed double carbonylation of o-dihaloarenes with amines in phosphonium salt ionic liquids proceeds efficiently to give the corresponding N-substituted phthalimides. This process can tolerate a wide array of functional groups and affords ...

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

  Synthesis of Chromones via Palladium-Catalyzed Ligand-Free Cyclocarbonylation of o-Iodophenols with Terminal Acetylenes in Phosphonium Salt Ionic Liquids

  Qian Yang and Howard Alper
  The Journal of Organic Chemistry2010 75 (3), 948-950

  • Synthesis of Chromones via Palladium-Catalyzed Ligand-Free Cyclocarbonylation of o-Iodophenols with Terminal Acetylenes in Phosphonium Salt Ionic Liquids

    Qian Yang and Howard Alper
    The Journal of Organic Chemistry2010 75 (3), 948-950

    The highly efficient and selective palladium-catalyzed ligand-free cyclocarbonylation reaction of o-iodophenols with terminal acetylenes and CO in the phosphonium salt ionic liquid, C14H29(C6H13)3P+Br−, affords diversified chromones in good to excellent ...

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

  Tetraalkylphosphonium Trihalides. Room Temperature Ionic Liquids As Halogenation Reagents

  Rodrigo Cristiano, Kefeng Ma, George Pottanat and Richard G. Weiss
  The Journal of Organic Chemistry2009 74 (23), 9027-9033

  • Tetraalkylphosphonium Trihalides. Room Temperature Ionic Liquids As Halogenation Reagents

    Rodrigo Cristiano, Kefeng Ma, George Pottanat and Richard G. Weiss
    The Journal of Organic Chemistry2009 74 (23), 9027-9033

    Six room temperature ionic liquids (RTILs) comprised of a tetraalkylphosphonium cation (tridecylmethyphosphonium or trihexyltetradecylphosphonium) and a trihalide anion (Br3−, BrCl2−, or ClBr2−) have been prepared and characterized. Their ability to ...

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

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