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Abstract

An efficient methodology for the indirect anti-Markovnikov hydration of unsymmetrically substituted terminal and internal alkynes is based on TiCl₄-catalyzed hydroamination reactions. Its application to ortho-alkynylhaloarenes, followed by a copper-catalyzed O-arylation, provides flexible access to substituted benzo[b]furans.

Citing Articles

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This article has been cited by 6 ACS Journal articles (5 most recent appear below).

• 

  Linear Polystyrene-Stabilized Palladium Nanoparticles-Catalyzed C–C Coupling Reaction in Water

  Atsushi Ohtaka, Takuto Teratani, Ryohei Fujii, Kanako Ikeshita, Takahiro Kawashima, Koichi Tatsumi, Osamu Shimomura, and Ryôki Nomura
  The Journal of Organic Chemistry2011 Article ASAP

  • Linear Polystyrene-Stabilized Palladium Nanoparticles-Catalyzed C–C Coupling Reaction in Water

    Atsushi Ohtaka, Takuto Teratani, Ryohei Fujii, Kanako Ikeshita, Takahiro Kawashima, Koichi Tatsumi, Osamu Shimomura, and Ryôki Nomura
    The Journal of Organic Chemistry2011 Article ASAP

    Linear polystyrene-stabilized PdO nanoparticles (PS-PdONPs) were prepared in water by thermal decomposition of Pd(OAc)2 in the presence of polystyrene. The immobilization degree of palladium was dependent on the molecular weight of polystyrene, while the ...

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

  Gold-Catalyzed Regioselective Hydration of Propargyl Acetates Assisted by a Neighboring Carbonyl Group: Access to α-Acyloxy Methyl Ketones and Synthesis of (±)-Actinopolymorphol B

  Nayan Ghosh, Sanatan Nayak, and Akhila K. Sahoo
  The Journal of Organic Chemistry2011 76 (2), 500-511

  • Gold-Catalyzed Regioselective Hydration of Propargyl Acetates Assisted by a Neighboring Carbonyl Group: Access to α-Acyloxy Methyl Ketones and Synthesis of (±)-Actinopolymorphol B

    Nayan Ghosh, Sanatan Nayak, and Akhila K. Sahoo
    The Journal of Organic Chemistry2011 76 (2), 500-511

    A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph3PAuCl and 1% AgSbF6 in dioxane−H2O ...

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

  Two Titanium-Catalyzed Reaction Sequences for Syntheses of Pyrroles from (E/Z)-Chloroenynes or α-Haloalkynols

  Lutz Ackermann, René Sandmann and Ludwig T. Kaspar
  Organic Letters2009 11 (9), 2031-2034

  • Two Titanium-Catalyzed Reaction Sequences for Syntheses of Pyrroles from (E/Z)-Chloroenynes or α-Haloalkynols

    Lutz Ackermann, René Sandmann and Ludwig T. Kaspar
    Organic Letters2009 11 (9), 2031-2034

    Titanium-catalyzed intermolecular hydroaminations of (E/Z)-chloroenynes enabled an efficient pyrrole synthesis, which set the stage for the development of a user-friendly one-pot reaction for the regioselective preparation of fully substituted pyrroles ...

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

  Efficient Synthesis of γ-Keto Esters through Neighboring Carbonyl Group-Assisted Regioselective Hydration of 3-Alkynoates

  Weibo Wang, Bo Xu and Gerald B. Hammond
  The Journal of Organic Chemistry2009 74 (4), 1640-1643

  • Efficient Synthesis of γ-Keto Esters through Neighboring Carbonyl Group-Assisted Regioselective Hydration of 3-Alkynoates

    Weibo Wang, Bo Xu and Gerald B. Hammond
    The Journal of Organic Chemistry2009 74 (4), 1640-1643

    The Au(III)-catalyzed hydration of 3-alkynoates led to a practical one-step synthesis of γ-keto esters in high yields, through a carbonyl group participation enabled by a favored 5-endodig cyclization. This mild-aqueous ethanol, room temperature, and ...

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

  A Novel Synthesis of 2-Functionalized Benzofurans by Palladium-Catalyzed Cycloisomerization of 2-(1-Hydroxyprop-2-ynyl)phenols Followed by Acid-Catalyzed Allylic Isomerization or Allylic Nucleophilic Substitution

  Bartolo Gabriele, Raffaella Mancuso and Giuseppe Salerno
  The Journal of Organic Chemistry2008 73 (18), 7336-7341

  • A Novel Synthesis of 2-Functionalized Benzofurans by Palladium-Catalyzed Cycloisomerization of 2-(1-Hydroxyprop-2-ynyl)phenols Followed by Acid-Catalyzed Allylic Isomerization or Allylic Nucleophilic Substitution

    Bartolo Gabriele, Raffaella Mancuso and Giuseppe Salerno
    The Journal of Organic Chemistry2008 73 (18), 7336-7341

    A novel two-step synthesis of 2-hydroxymethylbenzofurans 3 and 2-alkoxymethylbenzofurans 4−6, based on palladium-catalyzed cycloisomerization of 2-(1-hydroxyprop-2-ynyl)phenols 1 under basic conditions to give 2-methylene-2,3-dihydrobenzofuran-3-ols 2, ...

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

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