Radical Hydroxyalkylation of C−H Bond Adjacent to Nitrogen of Tertiary Amides, Ureas, and Amines

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Abstract

Tertiary amides, ureas, and amines undergo direct intermolecular addition to aldehydes under the Et₃B/air conditions, thereby providing a unique and simple means for the radical sp³ C−H transformation of nitrogen-containing molecules.

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This article has been cited by 9 ACS Journal articles (5 most recent appear below).

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  Regioselective Insertion of Carborynes into Ethereal C−H Bond: Facile Synthesis of α-Carboranylated Ethers

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  Journal of the American Chemical Society2011 133 (15), 5760-5763

  • Regioselective Insertion of Carborynes into Ethereal C−H Bond: Facile Synthesis of α-Carboranylated Ethers

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    Journal of the American Chemical Society2011 133 (15), 5760-5763

    Carborynes can exist in two resonance forms, bonding form vs biradical form. The biradical form can be readily generated via the elimination of LiI from 1-iodo-n-lithio-1,n-C2B10H10 (n = 2, 7) under UV irradiation. They can undergo α-C−H bond insertion ...

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

  Total Synthesis of (±)-Kainic Acid: A Photochemical C–H Carbamoylation Approach

  Takuma Kamon, Yayoi Irifune, Tetsuaki Tanaka, and Takehiko Yoshimitsu
  Organic Letters2011 Article ASAP

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    Organic Letters2011 Article ASAP

    A novel photochemical C–H carbamoylation of an octahydroisoindole derivative with PhNCO has allowed the authors to provide a unique access to a highly functionalized proline motif from which total synthesis of (±)-kainic acid, a bioactive marine alkaloid, ...

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• 

  Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover

  Gregory K. Friestad and Yaoping Wu
  Organic Letters2009 11 (4), 819-822

  • Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover

    Gregory K. Friestad and Yaoping Wu
    Organic Letters2009 11 (4), 819-822

    A carbon−carbon bond construction method is disclosed which involves radical addition of α-haloesters or iodoacetonitrile to enamides. Despite the presence of tri-n-butylstannane, nonreductive addition was predominant; H-atom transfer from tin hydride ...

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

  Chemoselective Conjugate Addition of Dimethylzinc-Mediated Ether and Acetal Radicals to Alkylidenemalonates and Asymmetric Reactions

  Ken-ichi Yamada, Masaru Maekawa, Tito Akindele, Mayu Nakano, Yasutomo Yamamoto and Kiyoshi Tomioka
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  • Chemoselective Conjugate Addition of Dimethylzinc-Mediated Ether and Acetal Radicals to Alkylidenemalonates and Asymmetric Reactions

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    The Journal of Organic Chemistry2008 73 (24), 9535-9538

    Cyclic and acyclic ether or acetal radicals were generated directly from ethers or acetals by the action of dimethylzinc−air, and their subsequent conjugate addition reaction with alkylidenemalonates afforded the corresponding conjugate adducts in ...

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• 

  Synthesis of Fused Piperidinones through a Radical-Ionic Cascade

  Edouard Godineau, Kurt Schenk and Yannick Landais
  The Journal of Organic Chemistry2008 73 (18), 6983-6993

  • Synthesis of Fused Piperidinones through a Radical-Ionic Cascade

    Edouard Godineau, Kurt Schenk and Yannick Landais
    The Journal of Organic Chemistry2008 73 (18), 6983-6993

    Azabicyclo[4.3.0]nonanes were assembled, from chiral allylsilanes possessing an oxime moiety, using a stereocontrolled formal [2 + 2 + 2] radical-ionic process. The cascade involves the addition of an α-iodoester to the less substituted end of the ...

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

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