Tin-Free Giese Reaction and the Related Radical Carbonylation Using Alkyl Iodides and Cyanoborohydrides

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Abstract

Tin-free Giese reaction and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. The reaction took place chemoselectively at the carbon−iodine bond but not at the carbon−bromine and carbon−chlorine bonds. The iodine atom transfer followed by hydride reduction of the resulting carbon−iodine bond is proposed as a possible mechanism.

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

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  • Radical Addition of Alkyl Halides to Formaldehyde in the Presence of Cyanoborohydride as a Radical Mediator. A New Protocol for Hydroxymethylation Reaction

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    Hydroxymethylation of alkyl halides was achieved using paraformaldehyde as a radical C1 synthon in the presence of tetrabutylammonium cyanoborohydride as a hydrogen source. The reaction proceeds via a radical chain mechanism involving an alkyl radical ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
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  Ex Vivo Oxidation in Tissue and Plasma Assays of Hydroxyoctadecadienoates: Z,E/E,E Stereoisomer Ratios

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

  Black-Light-Induced Radical/Ionic Hydroxymethylation of Alkyl Iodides with Atmospheric CO in the Presence of Tetrabutylammonium Borohydride

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    Shoji Kobayashi, Takuji Kawamoto, Shohei Uehara, Takahide Fukuyama and Ilhyong Ryu
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    Tin-free radical/ionic hydroxymethylation of secondary and tertiary alkyl iodides proceeded efficiently in the presence of tetrabutylammonium borohydride as the hydrogen source under atmospheric pressure of CO in conjunction with photoirradiation using ...

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

  EPR Studies of the Generation, Structure, and Reactivity of N-Heterocyclic Carbene Borane Radicals

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  • EPR Studies of the Generation, Structure, and Reactivity of N-Heterocyclic Carbene Borane Radicals

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    N-Heterocyclic carbene boranes (NHC−boranes) are a new “clean” class of reagents suitable for reductive radical chain transformations. Their structures are well suited for their reactivity to be tuned by inclusion of different NHC ring units and by ...

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

  Complexes of Borane and N-Heterocyclic Carbenes: A New Class of Radical Hydrogen Atom Donor

  Shau-Hua Ueng, Malika Makhlouf Brahmi, Étienne Derat, Louis Fensterbank, Emmanuel Lacôte, Max Malacria and Dennis P. Curran
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  • Complexes of Borane and N-Heterocyclic Carbenes: A New Class of Radical Hydrogen Atom Donor

    Shau-Hua Ueng, Malika Makhlouf Brahmi, Étienne Derat, Louis Fensterbank, Emmanuel Lacôte, Max Malacria and Dennis P. Curran
    Journal of the American Chemical Society2008 130 (31), 10082-10083

    Calculations suggest that complexes of borane with N-heterocyclic carbenes (NHC) have B−H bond dissocation energies more then 20 kcal/mol less than free borane, diborane, borane−THF, and related complexes. Values are in the range of popular radical ...

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

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