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Arylation

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Keith Fagnou – 1st expert on this subject based on the ideXlab platform

  • palladium catalyzed direct Arylation of azine and azole n oxides reaction development scope and applications in synthesis
    Journal of the American Chemical Society, 2009
    Co-Authors: Louischarles Campeau, David R Stuart, Jeanphilippe Leclerc, Megan Bertrandlaperle, Elisia Villemure, Sandrine Lasserre, Nicolas Guimond, Melanie Lecavallier, Keith Fagnou

    Abstract:

    Palladium-catalyzed direct Arylation reactions are described with a broad range of azine and azole N-oxides. In addition to aspects of functional group compatibility, issues of regioselectivity have been explored when nonsymmetrical azine N-oxides are used. In these cases, both the choice of ligand and the nature of the azine substituents play important roles in determining the regioisomeric distribution. When azole N-oxides are employed, preferential reaction is observed for Arylation at C2 which occurs under very mild conditions. Subsequent reactions are observed to occur at C5 followed by Arylation at C4. The potential utility of this methodology is illustrated by its use in the synthesis of a potent sodium channel inhibitor 1 and a Tie2 Tyrosine Kinase inhibitor 2.

  • site selective sp2 and benzylic sp3 palladium catalyzed direct Arylation
    Journal of the American Chemical Society, 2008
    Co-Authors: Louischarles Campeau, Derek J Schipper, Keith Fagnou

    Abstract:

    Palladium-catalyzed site selective Arylation reactions of both sp2 and benzylic sp3 sites on azine and diazine N-oxide substrates are described that occur in good to excellent yield and with complete selectivity for reaction at the desired position. These studies have uncovered the need to properly control the metal to ligand ratio in sp2 Arylation and necessitated a complete reinvestigation of all reaction parameters for sp3 Arylation. From these studies, the choice of base emerged as a pivotal component for site selectivity, pointing to its intimate involvement in the mechanism of direct Arylation. These site selective reactions have been validated in both divergent and sequential derivatizations of heterocyclic compounds represent an attractive alternative to other routes to this class of molecule.

  • palladium catalyzed benzene Arylation incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design
    Journal of the American Chemical Society, 2006
    Co-Authors: Marc Lafrance, Keith Fagnou

    Abstract:

    A palladium−pivalic acid cocatalyst system has been developed that exhibits unprecedented reactivity in direct Arylation. This reactivity is illustrated with the first examples of high yielding direct metalation−Arylation reactions of a completely unactivated arene, benzene. Experimental and computational evidence indicates that the pivalate anion is a key component in the palladation/C−H bond breaking event, that it lowers the energy of C−H bond cleavage and acts as a catalytic proton shuttle from benzene to the stoichiometric carbonate base. Eight examples of substituted aryl bromides are included which undergo direct Arylation with benzene in 55−85% yield.

Louischarles Campeau – 2nd expert on this subject based on the ideXlab platform

  • palladium catalyzed direct Arylation of azine and azole n oxides reaction development scope and applications in synthesis
    Journal of the American Chemical Society, 2009
    Co-Authors: Louischarles Campeau, David R Stuart, Jeanphilippe Leclerc, Megan Bertrandlaperle, Elisia Villemure, Sandrine Lasserre, Nicolas Guimond, Melanie Lecavallier, Keith Fagnou

    Abstract:

    Palladium-catalyzed direct Arylation reactions are described with a broad range of azine and azole N-oxides. In addition to aspects of functional group compatibility, issues of regioselectivity have been explored when nonsymmetrical azine N-oxides are used. In these cases, both the choice of ligand and the nature of the azine substituents play important roles in determining the regioisomeric distribution. When azole N-oxides are employed, preferential reaction is observed for Arylation at C2 which occurs under very mild conditions. Subsequent reactions are observed to occur at C5 followed by Arylation at C4. The potential utility of this methodology is illustrated by its use in the synthesis of a potent sodium channel inhibitor 1 and a Tie2 Tyrosine Kinase inhibitor 2.

  • site selective sp2 and benzylic sp3 palladium catalyzed direct Arylation
    Journal of the American Chemical Society, 2008
    Co-Authors: Louischarles Campeau, Derek J Schipper, Keith Fagnou

    Abstract:

    Palladium-catalyzed site selective Arylation reactions of both sp2 and benzylic sp3 sites on azine and diazine N-oxide substrates are described that occur in good to excellent yield and with complete selectivity for reaction at the desired position. These studies have uncovered the need to properly control the metal to ligand ratio in sp2 Arylation and necessitated a complete reinvestigation of all reaction parameters for sp3 Arylation. From these studies, the choice of base emerged as a pivotal component for site selectivity, pointing to its intimate involvement in the mechanism of direct Arylation. These site selective reactions have been validated in both divergent and sequential derivatizations of heterocyclic compounds represent an attractive alternative to other routes to this class of molecule.

  • palladium catalyzed direct Arylation of simple arenes in synthesis of biaryl molecules
    Chemical Communications, 2006
    Co-Authors: Louischarles Campeau, Keith Fagnou

    Abstract:

    Significant progress has been made in the direct Arylation of simple arenes. A number of catalyst systems have been developed which enable the intramolecular direct Arylation of aryl chlorides, bromides and iodides in high yield as well as conditions capable of achieving intermolecular direct Arylation with simple arenes. This account describes recent progress by our group and others in the development of these reactions.

Masahiro Miura – 3rd expert on this subject based on the ideXlab platform

  • transition metal catalyzedregioselective Arylation and vinylation of carboxylicacids
    Synthesis, 2010
    Co-Authors: Tetsuya Satoh, Masahiro Miura

    Abstract:

    Arene and heteroarene carboxylic acids undergo regioselectiveArylation and vinylation reactions at the positions ORTHO ( CINE)and IPSO to their carboxyl function undertransition-metal catalysis; these reactions are accompanied by carbon-hydrogenand carbon-carbon bond cleavages, respectively. Recentprogress in this area is summarized in this article. 1 Introduction 2 ORTHO- ( CINE-)Arylation 3 ORTHO- ( CINE-)Vinylation 4 IPSO-Arylation 5 IPSO-Vinylation 6 Conclusions

  • Nickel-Catalyzed Direct Arylation of Azoles with Aryl Bromides
    Organic Letters, 2009
    Co-Authors: Hitoshi Hachiya, Koji Hirano, Tetsuya Satoh, Masahiro Miura

    Abstract:

    Nickel catalyst systems for the direct C2 Arylation of oxazoles and thiazoles have been developed. The catalyst systems are cost-efficient and allow the use of various aryl bromides in the C−H Arylation of azoles.

  • rhodium catalyzed Arylation using arylboron compounds efficient coupling with aryl halides and unexpected multiple Arylation of benzonitrile
    Organic Letters, 2005
    Co-Authors: Kenji Ueura, And Tetsuya Satoh, Masahiro Miura

    Abstract:

    The Suzuki−Miyaura-type cross-coupling of arylboron compounds with aryl halides proceeds efficiently in the presence of a rhodium-based catalyst system to produce the corresponding biaryls. Furthermore, it has unexpectedly been observed that the treatment with benzonitrile under similar conditions brings about its multiple Arylation, in which nucleophilic Arylation on the cyano group and subsequent ortho Arylation via C−H bond cleavage are involved.