Easily Accessible and Highly Tunable Indolyl Phosphine Ligands for Suzuki−Miyaura Coupling of Aryl Chlorides

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Abstract

This study describes a new class of easily accessible indolyl phosphine ligands, prepared via an efficient protocol involving Fischer indolization from readily available phenylhydrazine and substituted acetophenones. This versatile ligand scaffold provides beneficial features, including high potential of steric and electronic tunability. The air-stable indolyl phosphines in combination with a palladium metal precursor provide highly effective catalysts for Suzuki−Miyaura coupling of unactivated aryl chlorides, and the catalyst loading down to 0.02 mol % can be achieved.

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This article has been cited by 11 ACS Journal articles (5 most recent appear below).

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  Ruthenium Complexes of κ(P)- and κ(P)-η⁶-Coordinated KITPHOS Monophosphines: Efficient Catalysts for the Direct Ortho Arylation of 2-Phenylpyridine and N-Phenylpyrazole with Aryl Chlorides

  Simon Doherty, Julian G. Knight, Carrie R. Addyman, Catherine H. Smyth, Nicholas A. B. Ward, and Ross W. Harrington
  Organometallics2011 30 (21), 6010-6016

  • Ruthenium Complexes of κ(P)- and κ(P)-η⁶-Coordinated KITPHOS Monophosphines: Efficient Catalysts for the Direct Ortho Arylation of 2-Phenylpyridine and N-Phenylpyrazole with Aryl Chlorides

    Simon Doherty, Julian G. Knight, Carrie R. Addyman, Catherine H. Smyth, Nicholas A. B. Ward, and Ross W. Harrington
    Organometallics2011 30 (21), 6010-6016

    Thermolysis of the P-coordinated KITPHOS monophosphine complex [(p-cymene)RuCl2(KITPHOS)] in chlorobenzene at 120 °C resulted in displacement of the p-cymene to afford [{κ(P)-η6-KITPHOS}RuCl2], the first example of a constrained-geometry complex in which ...

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

  Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

  Ranjan Jana, Tejas P. Pathak, and Matthew S. Sigman
  Chemical Reviews2011 111 (3), 1417-1492

  • Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

    Ranjan Jana, Tejas P. Pathak, and Matthew S. Sigman
    Chemical Reviews2011 111 (3), 1417-1492
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  A Novel, Air-Stable Phosphine Ligand for the Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reaction of Chloro Arenes

  Raju Ghosh, N. N. Adarsh and Amitabha Sarkar
  The Journal of Organic Chemistry2010 75 (15), 5320-5322

  • A Novel, Air-Stable Phosphine Ligand for the Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reaction of Chloro Arenes

    Raju Ghosh, N. N. Adarsh and Amitabha Sarkar
    The Journal of Organic Chemistry2010 75 (15), 5320-5322

    A novel, air-stable phosphine ligand, prepared from readily available 2-bromonitrobenzene and vinylmagnesium bromide, combines with Pd(CH3CN)2Cl2 to afford an effective catalyst for Suzuki−Miyaura cross-coupling of aryl, heteroaryl, and allyl chlorides ...

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

  Synthesis, Structures, and Characterizations of [ArTi(O-i-Pr)₃]₂ and Efficient Room-Temperature Aryl−Aryl Coupling of Aryl Bromides with [ArTi(O-i-Pr)₃]₂ Catalyzed by the Economic Pd(OAc)₂/PCy₃ System

  Hsu-Tang Yang, Shuangliu Zhou, Feng-Shuo Chang, Chi-Ren Chen and Han-Mou Gau
  Organometallics2009 28 (19), 5715-5721

  • Synthesis, Structures, and Characterizations of [ArTi(O-i-Pr)₃]₂ and Efficient Room-Temperature Aryl−Aryl Coupling of Aryl Bromides with [ArTi(O-i-Pr)₃]₂ Catalyzed by the Economic Pd(OAc)₂/PCy₃ System

    Hsu-Tang Yang, Shuangliu Zhou, Feng-Shuo Chang, Chi-Ren Chen and Han-Mou Gau
    Organometallics2009 28 (19), 5715-5721

    The series of aryltris(2-propoxo)titanium reagents [ArTi(O-i-Pr)3]2 (Ar = Ph (1a), 2-MeC6H4 (1b), 4-MeC6H4 (1c), 4-ClC6H4 (1d), 4-TMSC6H4 (1e), 4-CF3C6H4 (1f), 3,5-Me2C6H3 (1g)) was synthesized from reactions of the in situ prepared ClTi(O-i-Pr)3 with ...

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

  Suzuki−Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides

  Spencer D. Dreher, Siang-Ee Lim, Deidre L. Sandrock and Gary A. Molander
  The Journal of Organic Chemistry2009 74 (10), 3626-3631

  • Suzuki−Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides

    Spencer D. Dreher, Siang-Ee Lim, Deidre L. Sandrock and Gary A. Molander
    The Journal of Organic Chemistry2009 74 (10), 3626-3631

    Parallel microscale experimentation was used to develop general conditions for the Suzuki−Miyaura cross-coupling of diversely functionalized primary alkyltrifluoroborates with a variety of aryl chlorides. These conditions were found to be amenable to ...

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

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