Ruthenium-Catalyzed Cycloaddition of Aryl Azides and Alkynes

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Abstract

The formation of 1,5-disubstituted 1,2,3-triazoles from aryl azides and alkynes was readily accomplished using [Cp*RuCl]₄ catalyst in dimethylformamide. It was also demonstrated that the reaction provided higher yields, cleaner product, and shorter reaction times when carried out under microwave irradiation.

Citing Articles

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This article has been cited by 17 ACS Journal articles (5 most recent appear below).

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  Coordinatively Unsaturated Ruthenium Complexes As Efficient Alkyne–Azide Cycloaddition Catalysts

  Marina Lamberti, George C. Fortman, Albert Poater, Julie Broggi, Alexandra M. Z. Slawin, Luigi Cavallo, and Steven P. Nolan
  Organometallics2012 31 (2), 756-767

  • Coordinatively Unsaturated Ruthenium Complexes As Efficient Alkyne–Azide Cycloaddition Catalysts

    Marina Lamberti, George C. Fortman, Albert Poater, Julie Broggi, Alexandra M. Z. Slawin, Luigi Cavallo, and Steven P. Nolan
    Organometallics2012 31 (2), 756-767

    The performance of 16-electron ruthenium complexes with the general formula Cp*Ru(L)X (in which L = phosphine or N-heterocyclic carbene ligand; X = Cl or OCH2CF3) was explored in azide–alkyne cycloaddition reactions that afford the 1,2,3-triazole ...

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

  Synthesis and Computational Analysis of Densely Functionalized Triazoles Using o-Nitrophenylalkynes

  Melissa L. McIntosh, Ryne C. Johnston, Ommidala Pattawong, Bradley O. Ashburn, Michael R. Naffziger, Paul Ha-Yeon Cheong, and Rich G. Carter
  The Journal of Organic Chemistry2012 77 (2), 1101-1112

  • Synthesis and Computational Analysis of Densely Functionalized Triazoles Using o-Nitrophenylalkynes

    Melissa L. McIntosh, Ryne C. Johnston, Ommidala Pattawong, Bradley O. Ashburn, Michael R. Naffziger, Paul Ha-Yeon Cheong, and Rich G. Carter
    The Journal of Organic Chemistry2012 77 (2), 1101-1112

    Dipolar cylcoadditions with azides using a series of o-nitrophenylethynes and disubstituted alkynes were studied experimentally and computationally. Density functional theory computations reveal the steric and electronic parameters that control the ...

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

  Cu(I)- and Ru(II)-Mediated “Click” Cyclization of Tripeptides Toward Vancomycin-Inspired Mimics

  Jinqiang Zhang, Johan Kemmink, Dirk T. S. Rijkers, and Rob M. J. Liskamp
  Organic Letters2011 Article ASAP

  • Cu(I)- and Ru(II)-Mediated “Click” Cyclization of Tripeptides Toward Vancomycin-Inspired Mimics

    Jinqiang Zhang, Johan Kemmink, Dirk T. S. Rijkers, and Rob M. J. Liskamp
    Organic Letters2011 Article ASAP

    Structural mimics comprising 1,4- and 1,5-disubstituted triazole-containing cyclic tripeptides with excellent resemblance toward the DE-ring of vancomycin are conveniently accessible using Cu(I)- or Ru(II)-assisted “click” cyclization.

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

  Beyond Click-Chemistry: Transformation of Azides with Cyclopentadienyl Ruthenium Complexes

  Julie Risse, Rosario Scopelliti, and Kay Severin
  Organometallics2011 Article ASAP

  • Beyond Click-Chemistry: Transformation of Azides with Cyclopentadienyl Ruthenium Complexes

    Julie Risse, Rosario Scopelliti, and Kay Severin
    Organometallics2011 Article ASAP

    The cyclopentadienyl Ru complexes Cp*RuCl(cod) (cod = 1,5-cyclooctadiene), Cp*RuCl(PPh3)2, and [CpRuCl2]2 (Cp = η5-1-methoxy-2,4-di-tert-butyl-3-neopentylcyclopentadienyl) are able to catalyze the decomposition of benzyl azides to give 1,3,5-triphenyl-2,...

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• 

  Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide

  Johan R. Johansson, Per Lincoln, Bengt Nordén, and Nina Kann
  The Journal of Organic Chemistry2011 76 (7), 2355-2359

  • Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide

    Johan R. Johansson, Per Lincoln, Bengt Nordén, and Nina Kann
    The Journal of Organic Chemistry2011 76 (7), 2355-2359

    An experimentally simple sequential one-pot RuAAC reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields starting from an alkyl halide, sodium azide, and an alkyne, is reported. The organic azide is formed in situ by treating ...

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