Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl Iodides

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Abstract

Diaryliodonium salts have recently received considerable attention as mild arylation reagents in organic synthesis. This paper describes a regiospecific, sequential one-pot synthesis of symmetrical and unsymmetrical diaryliodonium tetrafluoroborates, which are the most popular salts in metal-catalyzed arylations. The protocol is fast and high-yielding and has a large substrate scope. Furthermore, the corresponding diaryliodonium triflates can conveniently be obtained via an in situ anion exchange.

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This article has been cited by 7 ACS Journal articles (5 most recent appear below).

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  Regiospecific Syntheses of Functionalized Diaryliodonium Tosylates via [Hydroxy(tosyloxy)iodo]arenes Generated in Situ from (Diacetoxyiodo)arenes

  Joong-Hyun Chun and Victor W. Pike
  The Journal of Organic Chemistry2012 Article ASAP

  • Regiospecific Syntheses of Functionalized Diaryliodonium Tosylates via [Hydroxy(tosyloxy)iodo]arenes Generated in Situ from (Diacetoxyiodo)arenes

    Joong-Hyun Chun and Victor W. Pike
    The Journal of Organic Chemistry2012 Article ASAP

    Ready access to 18F-labeled aryl synthons is required for preparing novel radiotracers for molecular imaging with positron emission tomography. Diaryliodonium salts react with cyclotron-produced no-carrier-added [18F]fluoride ion to produce [18F]aryl ...

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

  Direct Arylation of Arene and N-Heteroarenes with Diaryliodonium Salts without the Use of Transition Metal Catalyst

  Jun Wen, Ruo-Yi Zhang, Shan-Yong Chen, Ji Zhang, and Xiao-Qi Yu
  The Journal of Organic Chemistry2012 77 (1), 766-771

  • Direct Arylation of Arene and N-Heteroarenes with Diaryliodonium Salts without the Use of Transition Metal Catalyst

    Jun Wen, Ruo-Yi Zhang, Shan-Yong Chen, Ji Zhang, and Xiao-Qi Yu
    The Journal of Organic Chemistry2012 77 (1), 766-771

    A novel and simple transition metal-free direct arylation of arene and N-heteroarenes with diaryliodonium salts has been developed. This cross-coupling reaction is promoted only by base and gives the desired products in moderate to good yields.

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

  Metal-Free Synthesis of Aryl Esters from Carboxylic Acids and Diaryliodonium Salts

  Tue B. Petersen, Rehan Khan, and Berit Olofsson
  Organic Letters2011 Article ASAP

  • Metal-Free Synthesis of Aryl Esters from Carboxylic Acids and Diaryliodonium Salts

    Tue B. Petersen, Rehan Khan, and Berit Olofsson
    Organic Letters2011 Article ASAP

    An efficient arylation of carboxylic acids with diaryliodonium salts has been developed, giving aryl esters in high yields within short reaction times for both aromatic and aliphatic substrates. The transition-metal-free conditions are compatible with a ...

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

  Room Temperature, Metal-Free Synthesis of Diaryl Ethers with Use of Diaryliodonium Salts

  Nazli Jalalian, Eloisa E. Ishikawa, Luiz F. Silva, Jr., and Berit Olofsson
  Organic Letters2011 13 (6), 1552-1555

  • Room Temperature, Metal-Free Synthesis of Diaryl Ethers with Use of Diaryliodonium Salts

    Nazli Jalalian, Eloisa E. Ishikawa, Luiz F. Silva, Jr., and Berit Olofsson
    Organic Letters2011 13 (6), 1552-1555

    A fast, high-yielding synthesis of diaryl ethers with use of mild and metal-free conditions has been developed. The scope includes bulky ortho-substituted diaryl ethers, which are difficult to obtain by metal-catalyzed protocols. Halo-substituents, ...

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

  Palladium-Catalyzed C−H Arylation of 2,5-Substituted Pyrroles

  Anna M. Wagner and Melanie S. Sanford
  Organic Letters2011 13 (2), 288-291

  • Palladium-Catalyzed C−H Arylation of 2,5-Substituted Pyrroles

    Anna M. Wagner and Melanie S. Sanford
    Organic Letters2011 13 (2), 288-291

    The palladium-catalyzed direct arylation of 2,5-substituted pyrrole derivatives with diaryliodonium salts to generate tri-, tetra-, and penta-substituted pyrrole products is described. The scope and limitations of these transformations are also ...

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