Direct Use of Allylic Alcohols for Platinum-Catalyzed Monoallylation of Amines

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Abstract

A new direct catalytic amination of allylic alcohols promoted by the combination of platinum and a large bite-angle ligand DPEphos was developed in which the allylic alcohol was effectively converted to a π-allylplatinum intermediate without the use of an activating reagent. The use of the DPEphos ligand was essential for obtaining high catalyst activity and high monoallylation selectivity of primary amines, allowing the formation of a variety of monoallylation products in good to excellent yield.

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This article has been cited by 15 ACS Journal articles (5 most recent appear below).

• 

  Direct Catalytic Azidation of Allylic Alcohols

  Magnus Rueping, Carlos Vila, and Uxue Uria
  Organic Letters2012 14 (3), 768-771

  • Direct Catalytic Azidation of Allylic Alcohols

    Magnus Rueping, Carlos Vila, and Uxue Uria
    Organic Letters2012 14 (3), 768-771

    A direct catalytic azidation of primary, secondary, and tertiary allylic alcohols has been developed. This new azidation reaction affords the corresponding allylic azides in high to excellent yields and regioselectivities. The reaction provides ...

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

  Palladium-Catalyzed Amination of Allyl Alcohols

  Raju Ghosh and Amitabha Sarkar
  The Journal of Organic Chemistry2011 76 (20), 8508-8512

  • Palladium-Catalyzed Amination of Allyl Alcohols

    Raju Ghosh and Amitabha Sarkar
    The Journal of Organic Chemistry2011 76 (20), 8508-8512

    An efficient catalytic amination of aryl-substituted allylic alcohols has been developed. The complex [(η3-allyl)PdCl]2 modified by a bis phosphine ligand, L, has been used as catalyst in the reaction that afforded a wide range of allyl amines in good to ...

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

  Palladium-Catalyzed Mono-N-allylation of Unprotected Anthranilic Acids with Allylic Alcohols in Aqueous Media

  Hidemasa Hikawa and Yuusaku Yokoyama
  The Journal of Organic Chemistry2011 76 (20), 8433-8439

  • Palladium-Catalyzed Mono-N-allylation of Unprotected Anthranilic Acids with Allylic Alcohols in Aqueous Media

    Hidemasa Hikawa and Yuusaku Yokoyama
    The Journal of Organic Chemistry2011 76 (20), 8433-8439

    Palladium-catalyzed N-allylation of anthranilic acids 1a–j with allyl alcohol 2a in the presence of Pd(OAc)2, sodium diphenylphosphinobenzene-3-sulfonate (TPPMS) in THF–H2O at room temperature gave only mono-N-allylated anthranilic acids 3a–j in good ...

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

  Discovery and Mechanistic Studies of a General Air-Promoted Metal-Catalyzed Aerobic N-Alkylation Reaction of Amides and Amines with Alcohols

  Chuanzhi Liu, Shiheng Liao, Qiang Li, Sunlin Feng, Qing Sun, Xiaochun Yu, and Qing Xu
  The Journal of Organic Chemistry2011 76 (14), 5759-5773

  • Discovery and Mechanistic Studies of a General Air-Promoted Metal-Catalyzed Aerobic N-Alkylation Reaction of Amides and Amines with Alcohols

    Chuanzhi Liu, Shiheng Liao, Qiang Li, Sunlin Feng, Qing Sun, Xiaochun Yu, and Qing Xu
    The Journal of Organic Chemistry2011 76 (14), 5759-5773

    The thermodynamically unfavorable anaerobic dehydrogenative alcohol activation to aldehydes and hydridometal species is found to be the bottleneck in metal-catalyzed N-alkylations due to a general and unnoticed catalyst deactivation by amines/amides. Thus,...

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

  Chirality Transfer in Au-Catalyzed Cyclization Reactions of Monoallylic Diols: Selective Access to Specific Enantiomers Based on Olefin Geometry

  Aaron Aponick and Berenger Biannic
  Organic Letters2011 13 (6), 1330-1333

  • Chirality Transfer in Au-Catalyzed Cyclization Reactions of Monoallylic Diols: Selective Access to Specific Enantiomers Based on Olefin Geometry

    Aaron Aponick and Berenger Biannic
    Organic Letters2011 13 (6), 1330-1333

    The gold(I)-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is shown to be highly stereoselective when chiral allylic alcohols are employed. Substrates that differ only in olefin geometry provide enantiomeric products from formal SN2′ ...

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