Palladium-Catalyzed Silylation of Aryl Chlorides with Hexamethyldisilane

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Abstract

A method for the palladium-catalyzed silylation of aryl chlorides has been developed. The method affords desired product in good yield, is tolerant of a variety of functional groups, and provides access to a wide variety of aryltrimethylsilanes from commercially available aryl chlorides. Additionally, a one-pot procedure that converts aryl chlorides into aryl iodides has been developed.

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This article has been cited by 4 ACS Journal articles (4 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
• 

  Microwave-Assisted Trans-Halogenation Reactions of Various Chloro-, Bromo-, Trifluoromethanesulfonyloxy- and Nonafluorobutanesulfonyloxy-Substituted Quinolines, Isoquinolines, and Pyridines Leading to the Corresponding Iodinated Heterocycles

  Alex C. Bissember and Martin G. Banwell
  The Journal of Organic Chemistry2009 74 (13), 4893-4895

  • Microwave-Assisted Trans-Halogenation Reactions of Various Chloro-, Bromo-, Trifluoromethanesulfonyloxy- and Nonafluorobutanesulfonyloxy-Substituted Quinolines, Isoquinolines, and Pyridines Leading to the Corresponding Iodinated Heterocycles

    Alex C. Bissember and Martin G. Banwell
    The Journal of Organic Chemistry2009 74 (13), 4893-4895

    Microwave irradiation of certain chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines in the presence of acetic anhydride and sodium iodide leads, via a trans-halogenation process, to the corresponding ...

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

  Direct and Selective Arylation of Tertiary Silanes with Rhodium Catalyst

  Yoshinori Yamanoi and Hiroshi Nishihara
  The Journal of Organic Chemistry2008 73 (17), 6671-6678

  • Direct and Selective Arylation of Tertiary Silanes with Rhodium Catalyst

    Yoshinori Yamanoi and Hiroshi Nishihara
    The Journal of Organic Chemistry2008 73 (17), 6671-6678
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Biphenylene-Substituted Ruthenocenylphosphine for Suzuki–Miyaura Coupling of Aryl Chlorides

  Takashi Hoshi, Taichi Nakazawa, Ippei Saitoh, Ayako Mori, Toshio Suzuki, Jun-ichi Sakai and Hisahiro Hagiwara
  Organic Letters2008 10 (10), 2063-2066

  • Biphenylene-Substituted Ruthenocenylphosphine for Suzuki–Miyaura Coupling of Aryl Chlorides

    Takashi Hoshi, Taichi Nakazawa, Ippei Saitoh, Ayako Mori, Toshio Suzuki, Jun-ichi Sakai and Hisahiro Hagiwara
    Organic Letters2008 10 (10), 2063-2066

    > High activity in the palladium-catalyzed Suzuki−Miyaura reactions of aryl chlorides with arylboronic acids was furnished using biphenylene-substituted di-tert-butylruthenocenylphosphine (R-Phos) as a supporting ligand. Substrate combinations even for ...

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

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