C-C Bond Formation

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Tomislav Rovis - One of the best experts on this subject based on the ideXlab platform.

  • amide directed photoredox catalysed c c Bond Formation at unactivated sp 3 c h Bonds
    Nature, 2016
    Co-Authors: Tomislav Rovis
    Abstract:

    The Formation of carbon–carbon Bonds is achieved via directed cleavage of traditionally non-reactive carbon–hydrogen Bonds and their subsequent coupling with readily available alkenes. In two separate reports, Robert Knowles and colleagues, and John Chu and Tomislav Rovis report the selective homolysis of selected amidyl N–H Bonds through a photocatalytic proton-coupled electron-transfer process. The resulting radical enables C–H abstraction and radical alkylation at the unactivated 5 position on the aliphatic chain of the N-alkyl amide. As this method does not rely on pre-activation of the amidyl N–H Bond or the use of haloamides, it offers a potentially simpler solution than previous approaches to radical amidyls. Additionally, the subsequent 1,5-hydrogen-atom transfer offers a route to selective C–C Bond Formation in the presence of alkyl amides. Carbon–carbon (C–C) Bond Formation is paramount in the synthesis of biologically relevant molecules, modern synthetic materials and commodity chemicals such as fuels and lubricants. Traditionally, the presence of a functional group is required at the site of C–C Bond Formation. Strategies that allow C–C Bond Formation at inert carbon–hydrogen (C–H) Bonds enable access to molecules that would otherwise be inaccessible and the development of more efficient syntheses of complex molecules1,2. Here we report a method for the Formation of C–C Bonds by directed cleavage of traditionally non-reactive C–H Bonds and their subsequent coupling with readily available alkenes. Our methodology allows for amide-directed selective C–C Bond Formation at unactivated sp3 C–H Bonds in molecules that contain many such Bonds that are seemingly indistinguishable. Selectivity arises through a relayed photoredox-catalysed oxidation of a nitrogen–hydrogen Bond. We anticipate that our findings will serve as a starting point for functionalization at inert C–H Bonds through a strategy involving hydrogen-atom transfer.

  • Amide-directed photoredox-catalysed C–C Bond Formation at unactivated sp 3 C–H Bonds
    Nature, 2016
    Co-Authors: John C. K. Chu, Tomislav Rovis
    Abstract:

    Carbon-carbon (C-C) Bond Formation is paramount in the synthesis of biologically relevant molecules, modern synthetic materials and commodity chemicals such as fuels and lubricants. Traditionally, the presence of a functional group is required at the site of C-C Bond Formation. Strategies that allow C-C Bond Formation at inert carbon-hydrogen (C-H) Bonds enable access to molecules that would otherwise be inaccessible and the development of more efficient syntheses of complex molecules. Here we report a method for the Formation of C-C Bonds by directed cleavage of traditionally non-reactive C-H Bonds and their subsequent coupling with readily available alkenes. Our methodology allows for amide-directed selective C-C Bond Formation at unactivated sp3 C-H Bonds in molecules that contain many such Bonds that are seemingly indistinguishable. Selectivity arises through a relayed photoredox-catalysed oxidation of a nitrogen-hydrogen Bond. We anticipate that our findings will serve as a starting point for functionalization at inert C-H Bonds through a strategy involving hydrogen-atom transfer.

Gedu Satyanarayana - One of the best experts on this subject based on the ideXlab platform.

Zhangjie Shi - One of the best experts on this subject based on the ideXlab platform.

  • transition metal catalyzed c c Bond Formation through the fixation of carbon dioxide
    Chemical Society Reviews, 2011
    Co-Authors: Ku Huang, Zhangjie Shi
    Abstract:

    Carbon dioxide is an important carbon source in the atmosphere and is “problematic” toward the activities of human beings. Although carbon dioxide is a cheap, abundant and relatively nontoxic C1 source, its chemical transFormations have not been widely developed so far and are still far from synthetic applications, especially in the construction of the C–C Bond. This critical review summarizes the recent advances on transition-metal-catalyzed C–C Bond Formation through the fixation of carbon dioxide and their synthetic applications (124 references).

  • Transition-metal-catalyzed C–C Bond Formation through the fixation of carbon dioxide
    Chemical Society reviews, 2011
    Co-Authors: Kun Huang, Chang‐liang Sun, Zhangjie Shi
    Abstract:

    Carbon dioxide is an important carbon source in the atmosphere and is “problematic” toward the activities of human beings. Although carbon dioxide is a cheap, abundant and relatively nontoxic C1 source, its chemical transFormations have not been widely developed so far and are still far from synthetic applications, especially in the construction of the C–C Bond. This critical review summarizes the recent advances on transition-metal-catalyzed C–C Bond Formation through the fixation of carbon dioxide and their synthetic applications (124 references).

Pedireddi Niharika - One of the best experts on this subject based on the ideXlab platform.

Hui Chen - One of the best experts on this subject based on the ideXlab platform.