N-Heterocyclic Carbene (NHC)-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds

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Abstract

NHC-catalyzed direct amidation of aldehydes with nitroso compounds is a powerful method for the synthesis of N-arylhydroxamic acids. A variety of aryl, alkyl, alkenyl, and heterocyclic aldehydes were found to give excellent yields of the corresponding N-arylhydroxamic acids. This chemistry was also extended to the synthesis of chiral N-arylhydroxamic acids by kinetic resolution of α-branched aldehydes, a domino amidation−redox amination reaction of acrolein, and a three-component reaction for the synthesis of N-arylaziridines.

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

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  Enantioselective N-Heterocyclic Carbene-Catalyzed Michael Addition to α,β-Unsaturated Aldehydes by Redox Oxidation

  Zi-Qiang Rong, Min-Qiang Jia, and Shu-Li You
  Organic Letters2011 Article ASAP

  • Enantioselective N-Heterocyclic Carbene-Catalyzed Michael Addition to α,β-Unsaturated Aldehydes by Redox Oxidation

    Zi-Qiang Rong, Min-Qiang Jia, and Shu-Li You
    Organic Letters2011 Article ASAP

    Enantioselective N-heterocyclic carbene-catalyzed Michael addition reactions to α,β-unsaturated aldehydes by redox oxidation were realized. With 10 mol % of camphor-derived triazolium salt D, 15 mol % of DBU, 5 mol % of NaBF4, and 100 mol % of quinone ...

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• 

  N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aldehydes with Arylsulfonyl Indoles

  Yi Li, Fu-Qiang Shi, Qing-Li He and Shu-Li You
  Organic Letters2009 11 (15), 3182-3185

  • N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aldehydes with Arylsulfonyl Indoles

    Yi Li, Fu-Qiang Shi, Qing-Li He and Shu-Li You
    Organic Letters2009 11 (15), 3182-3185

    3-(1-Arylsulfonylalkyl)indoles as electrophiles in the N-heterocyclic carbene-catalyzed umpolung reaction of aldehydes were realized for the first time. This intermolecular Stetter-type reaction features the commercially available catalyst and mild ...

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

  Synthesis of Fluoroalkene Dipeptide Isosteres by an Intramolecular Redox Reaction Utilizing N-Heteorocyclic Carbenes (NHCs)

  Yoko Yamaki, Akira Shigenaga, Kenji Tomita, Tetsuo Narumi, Nobutaka Fujii and Akira Otaka
  The Journal of Organic Chemistry2009 74 (9), 3272-3277

  • Synthesis of Fluoroalkene Dipeptide Isosteres by an Intramolecular Redox Reaction Utilizing N-Heteorocyclic Carbenes (NHCs)

    Yoko Yamaki, Akira Shigenaga, Kenji Tomita, Tetsuo Narumi, Nobutaka Fujii and Akira Otaka
    The Journal of Organic Chemistry2009 74 (9), 3272-3277

    (Z)-Fluoroalkene dipeptide isosteres (FADIs 16) have served as potential dipeptide mimetics possessing the substitution of fluoroalkenes for parent peptide bonds. Previously, we synthesized FADIs by reduction of γ,γ-difluoro-α,β-enoates with ...

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

  Single-Flask Synthesis of N-Acylated Indoles by Catalytic Dehydrogenative Coupling with Primary Alcohols

  Brooks E. Maki and Karl A. Scheidt
  Organic Letters2009 11 (7), 1651-1654

  • Single-Flask Synthesis of N-Acylated Indoles by Catalytic Dehydrogenative Coupling with Primary Alcohols

    Brooks E. Maki and Karl A. Scheidt
    Organic Letters2009 11 (7), 1651-1654

    Indoles and alcohols can be coupled in a dehydrogenative process catalyzed by tetrapropylammonium perruthenate. This efficient approach to indolylamides proceeds in a single flask under mild conditions. By employing substituted indoles and alkyl, ...

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• 

  N-Heterocyclic Carbene Catalyzed Ring Expansion of Formylcyclopropanes: Synthesis of 3,4-Dihydro-α-pyrone Derivatives

  Gong-Qiang Li, Li-Xin Dai and Shu-Li You
  Organic Letters2009 11 (7), 1623-1625

  • N-Heterocyclic Carbene Catalyzed Ring Expansion of Formylcyclopropanes: Synthesis of 3,4-Dihydro-α-pyrone Derivatives

    Gong-Qiang Li, Li-Xin Dai and Shu-Li You
    Organic Letters2009 11 (7), 1623-1625

    N-Heterocyclic carbene catalyzed ring expansion of readily accessible 2-acyl-1-formylcyclopropanes was developed. With 5 mol % of triazolium salt 5 and 30 mol % of DBU, ring expansion of various 2-acyl-1-formylcyclopropanes led to 3,4-dihydro-α-pyrones ...

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