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Abstract

We present results on the amidation of aryl halides and sulfonates utilizing a monodentate biaryl phosphine-Pd catalyst. Our results are in accord with a previous report that suggests that the formation of κ²-amidate complexes is deleterious to the effectiveness of a catalyst for this transformation and that their formation can be prevented by the use of appropriate bidentate ligands. We now provide data that suggest that the use of certain monodentate ligands can also prevent the formation of the κ²-amidate complexes and thereby generate more stable catalysts for the amination of aryl chlorides. Furthermore, computational studies shed light on the importance of the key feature(s) of the biaryl phosphines (a methyl group ortho to the phosphorus center) that enable the coupling to occur. The use of ligands that possess a methyl group ortho to the phosphorus center allows a variety of aryl and heteroaryl chlorides with various amides to be coupled in high yield.

Citing Articles

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This article has been cited by 37 ACS Journal articles (5 most recent appear below).

• 

  Characterization of Two Stable Degradants of Palladium ^tBuXPhos Catalyst and a Unique Dearomatization Reaction

  Alan M. Allgeier, Bradley J. Shaw, Tsang-Lin Hwang, Jacqueline E. Milne, Jason S. Tedrow, and Christopher N. Wilde
  Organometallics2012 31 (2), 519-522

  • Characterization of Two Stable Degradants of Palladium ^tBuXPhos Catalyst and a Unique Dearomatization Reaction

    Alan M. Allgeier, Bradley J. Shaw, Tsang-Lin Hwang, Jacqueline E. Milne, Jason S. Tedrow, and Christopher N. Wilde
    Organometallics2012 31 (2), 519-522

    Two stable degradants of palladium tBuXPhos catalyst have been synthesized from tBuXPhos and Pd2(dba)3·CHCl3, isolated, and fully characterized. Complex 2 augments the known literature examples of palladacycles from this ligand family but is present as a ...

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

  Completely N¹-Selective Palladium-Catalyzed Arylation of Unsymmetric Imidazoles: Application to the Synthesis of Nilotinib

  Satoshi Ueda, Mingjuan Su, and Stephen L. Buchwald
  Journal of the American Chemical Society2012 134 (1), 700-706

  • Completely N¹-Selective Palladium-Catalyzed Arylation of Unsymmetric Imidazoles: Application to the Synthesis of Nilotinib

    Satoshi Ueda, Mingjuan Su, and Stephen L. Buchwald
    Journal of the American Chemical Society2012 134 (1), 700-706

    The completely N1-selective Pd-catalyzed arylation of unsymmetric imidazoles with aryl halides and triflates is described. This study showed that imidazoles have a strong inhibitory effect on the in situ formation of the catalytically active Pd(0)–ligand ...

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

  Palladium-Catalyzed Arylation of Cyanamides

  Ryan M. Stolley, Wenxing Guo, and Janis Louie
  Organic Letters2012 14 (1), 322-325

  • Palladium-Catalyzed Arylation of Cyanamides

    Ryan M. Stolley, Wenxing Guo, and Janis Louie
    Organic Letters2012 14 (1), 322-325

    The cross-coupling of alkyl cyanamides with a number of aryl, heteroaryl, and vinyl halide and pseudohalide coupling partners has been developed via a modification of Pd-catalyzed amidation methods. The reactions proceed selectively under mild conditions ...

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

  A Simple Copper-Catalyzed Synthesis of Tertiary Acyclic Amides

  Emilie Racine, Florian Monnier, Jean-Pierre Vors, and Marc Taillefer
  Organic Letters2011 13 (11), 2818-2821

  • A Simple Copper-Catalyzed Synthesis of Tertiary Acyclic Amides

    Emilie Racine, Florian Monnier, Jean-Pierre Vors, and Marc Taillefer
    Organic Letters2011 13 (11), 2818-2821

    The N-arylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper catalytic system. The corresponding tertiary acyclic amides, which can be found in numerous ...

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

  A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates

  Shashank Shekhar, Travis B. Dunn, Brian J. Kotecki, Donna K. Montavon, and Steven C. Cullen
  The Journal of Organic Chemistry2011 76 (11), 4552-4563

  • A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates

    Shashank Shekhar, Travis B. Dunn, Brian J. Kotecki, Donna K. Montavon, and Steven C. Cullen
    The Journal of Organic Chemistry2011 76 (11), 4552-4563

    A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO4 in tert-amyl alcohol was found to be the optimal base–...

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

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