Aminocarbonylation of Aryl Halides Using a Nickel Phosphite Catalytic System

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Abstract

The nickel and phosphite catalytic system with sodium methoxide enables a very efficient aminocarbonylation reaction to be performed between aryl iodides or bromides and N,N-dimethylformamide (DMF). Phosphite ligand 1, which is very stable to air and moisture and, furthermore, inexpensive, afforded the highest reaction yield.

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

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  Palladium-Catalyzed Carbon-Monoxide-Free Aminocarbonylation of Aryl Halides Using N-Substituted Formamides as an Amide Source

  Dinesh N. Sawant, Yogesh S. Wagh, Kushal D. Bhatte, and Bhalchandra M. Bhanage
  The Journal of Organic Chemistry2011 Article ASAP

  • Palladium-Catalyzed Carbon-Monoxide-Free Aminocarbonylation of Aryl Halides Using N-Substituted Formamides as an Amide Source

    Dinesh N. Sawant, Yogesh S. Wagh, Kushal D. Bhatte, and Bhalchandra M. Bhanage
    The Journal of Organic Chemistry2011 Article ASAP

    A carbon-monoxide-free aminocarbonylation of various N-substituted formamides with aryl iodides and aryl bromides using palladium acetate and Xantphos is described. The developed methodology is applicable for a wide range of formamides and aryl halides ...

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

  Mo(CO)₆-Mediated Carbamoylation of Aryl Halides

  Wei Ren and Motoki Yamane
  The Journal of Organic Chemistry2010 75 (24), 8410-8415

  • Mo(CO)₆-Mediated Carbamoylation of Aryl Halides

    Wei Ren and Motoki Yamane
    The Journal of Organic Chemistry2010 75 (24), 8410-8415

    A simple method for the synthesis of amides has been developed by molybdenum-mediated carbamoylation of aryl halides. Whereas the conventional palladium-catalyzed three-component coupling reaction requires a large excess of gaseous carbon monoxide, the ...

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• 

  Carbamoylation of Aryl Halides by Molybdenum or Tungsten Carbonyl Amine Complexes

  Wei Ren and Motoki Yamane
  The Journal of Organic Chemistry2010 75 (9), 3017-3020

  • Carbamoylation of Aryl Halides by Molybdenum or Tungsten Carbonyl Amine Complexes

    Wei Ren and Motoki Yamane
    The Journal of Organic Chemistry2010 75 (9), 3017-3020

    When aryl halide is treated with molybdenum carbonyl amine complex in the presence of base, carbamoylation proceeds to give amide in good yield. The proposed mechanism involves oxidative addition of aryl halide to molybdenum(0) complex, migratory ...

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

  The Scope and Limitation of Nickel-Catalyzed Aminocarbonylation of Aryl Bromides from Formamide Derivatives

  Youngshin Jo, Jinhun Ju, Jaehoon Choe, Kwang Ho Song and Sunwoo Lee
  The Journal of Organic Chemistry2009 74 (16), 6358-6361

  • The Scope and Limitation of Nickel-Catalyzed Aminocarbonylation of Aryl Bromides from Formamide Derivatives

    Youngshin Jo, Jinhun Ju, Jaehoon Choe, Kwang Ho Song and Sunwoo Lee
    The Journal of Organic Chemistry2009 74 (16), 6358-6361

    Nickel-catalyzed aminocarbonylation of aryl halides is described. A well-defined air-stable nickel−phosphite catalytic system (Ni(OAc)2·4H2O/phosphite 1) effectively promoted the aminocarbonylation of aryl bromides with a range of formamides to give the ...

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

  Rh(I)-Catalyzed CO Gas-Free Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Using Formaldehyde

  Tsumoru Morimoto, Kae Yamasaki, Akihisa Hirano, Ken Tsutsumi, Natsuko Kagawa, Kiyomi Kakiuchi, Yasuyuki Harada, Yoshiya Fukumoto, Naoto Chatani and Takanori Nishioka
  Organic Letters2009 11 (8), 1777-1780

  • Rh(I)-Catalyzed CO Gas-Free Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Using Formaldehyde

    Tsumoru Morimoto, Kae Yamasaki, Akihisa Hirano, Ken Tsutsumi, Natsuko Kagawa, Kiyomi Kakiuchi, Yasuyuki Harada, Yoshiya Fukumoto, Naoto Chatani and Takanori Nishioka
    Organic Letters2009 11 (8), 1777-1780

    The rhodium(I)-catalyzed reaction of alkynes with 2-bromophenylboronic acids in the presence of paraformaldehyde resulted in a CO gas-free carbonylative cyclization, yielding indenone derivatives. [RhCl(BINAP)]2 and [RhCl(cod)]2 were responsible for the ...

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

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