Highly Efficient Pd-Catalyzed Carbonylative Cross-Coupling Reactions with Tetraorganoindates

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Abstract

Tetraorganoindates, which were prepared easily from the reaction of 1 equiv of InCl₃ with 4 equiv of organometallics, could be employed as effective nucleophilic cross-coupling partners in Pd-catalyzed carbonylative cross-coupling reactions with a variety of organic electrophiles. The present method gave unsymmetrical ketones and 1,4-diacylbenzenes in good yields with highly efficient transfer of almost all the organic groups attached to the indium under a carbon monoxide atmosphere in THF at 60 °C.

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This article has been cited by 12 ACS Journal articles (5 most recent appear below).

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  Substituted Butenylindium Generated by Transmetalation of Cyclopropylmethylstannane with Indium Iodide: Synthesis and Characterization of Monobutenylindium

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  Organometallics2011 30 (7), 2039-2043

  • Substituted Butenylindium Generated by Transmetalation of Cyclopropylmethylstannane with Indium Iodide: Synthesis and Characterization of Monobutenylindium

    Kensuke Kiyokawa, Makoto Yasuda, and Akio Baba
    Organometallics2011 30 (7), 2039-2043

    Transmetalation between substituted cyclopropylmethylstannanes and indium iodide provided the corresponding mono- and dibutenylindium species. The bulky substituent on a cyclopropyl ring selectively afforded the monobutenylindium species, which allowed ...

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

  Rh-Catalyzed Carbonylation of Arylzinc Compounds Yielding Symmetrical Diaryl Ketones by the Assistance of Oxidizing Agents

  Kana Kobayashi, Yugo Nishimura, Fuxing Gao, Kazuma Gotoh, Yasushi Nishihara, and Kentaro Takagi
  The Journal of Organic Chemistry2011 76 (6), 1949-1952

  • Rh-Catalyzed Carbonylation of Arylzinc Compounds Yielding Symmetrical Diaryl Ketones by the Assistance of Oxidizing Agents

    Kana Kobayashi, Yugo Nishimura, Fuxing Gao, Kazuma Gotoh, Yasushi Nishihara, and Kentaro Takagi
    The Journal of Organic Chemistry2011 76 (6), 1949-1952

    Carbonylative homocoupling of arylzinc compounds 1 using 1 atm of CO and 1,2-dibromoethane as an oxidant was achieved in the presence of Rh−dppf catalyst, affording symmetrical diaryl ketones in good yields. Under similar conditions, Pd or Ni catalysts ...

    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
• 

  Synthesis of Di-, Tri-, and Tetrasulfides through Multifold Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolates) in a One-Pot Procedure

  Phil Ho Lee, Youngchul Park, Sangkyun Park, Euijae Lee, and Sunggak Kim
  The Journal of Organic Chemistry2011 76 (3), 760-765

  • Synthesis of Di-, Tri-, and Tetrasulfides through Multifold Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolates) in a One-Pot Procedure

    Phil Ho Lee, Youngchul Park, Sangkyun Park, Euijae Lee, and Sunggak Kim
    The Journal of Organic Chemistry2011 76 (3), 760-765

    Pd-catalyzed multifold (2-, 3-, and 4-fold) carbon−sulfur cross-coupling reaction of indium tri(organothiolates) with polybromonated aromatic and heteroaromatic compounds was developed in a one-pot procedure. Both 2,5-dibromopyridine and 2,6-...

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

  Preparation of Ethyl 2-Aryl 2,3-Alkadienoates via Palladium-Catalyzed Selective Cross-Coupling Reactions

  Phil Ho Lee, Juntae Mo, Dongjin Kang, Dahan Eom, Chansoo Park, Chang-Hee Lee, Young Mee Jung, and Hyonseok Hwang
  The Journal of Organic Chemistry2011 76 (1), 312-315

  • Preparation of Ethyl 2-Aryl 2,3-Alkadienoates via Palladium-Catalyzed Selective Cross-Coupling Reactions

    Phil Ho Lee, Juntae Mo, Dongjin Kang, Dahan Eom, Chansoo Park, Chang-Hee Lee, Young Mee Jung, and Hyonseok Hwang
    The Journal of Organic Chemistry2011 76 (1), 312-315

    Pd-catalyzed cross-coupling reactions of aryl iodides containing not only an electron-donating group but also an electron-withdrawing group on the aryl ring with organoindium reagents generated in situ from indium and ethyl 4-bromo-2-alkynoates produced ...

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

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