Hydroarylation

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Ross A Widenhoefer - One of the best experts on this subject based on the ideXlab platform.

Hiroaki Ohno - One of the best experts on this subject based on the ideXlab platform.

Bradley D Robertson - One of the best experts on this subject based on the ideXlab platform.

Gojko Lalic - One of the best experts on this subject based on the ideXlab platform.

  • nickel catalyzed anti markovnikov Hydroarylation of alkenes
    Chemical Science, 2019
    Co-Authors: Julia Nguyen, Andrea Chong, Gojko Lalic
    Abstract:

    We have developed a nickel-catalyzed Hydroarylation of alkenes using aryl halides as coupling partners. Excellent anti-Markovnikov selectivity is achieved with aryl-substituted alkenes and enol ethers. We also show that Hydroarylation occurs with alkyl substituted alkenes to yield linear products. Preliminary examination of the reaction mechanism suggests irreversible hydrometallation as the selectivity determining step of the Hydroarylation.

  • diastereodivergent reductive cross coupling of alkynes through tandem catalysis z and e selective Hydroarylation of terminal alkynes
    Journal of the American Chemical Society, 2018
    Co-Authors: Megan K Armstrong, Madison B Goodstein, Gojko Lalic
    Abstract:

    A diastereodivergent Hydroarylation of terminal alkynes is accomplished using tandem catalysis. The Hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The Hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective Hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semireduction. The E-selective Hydroarylation involves an additional catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the Hydroarylation. Our studies also show that, although the Z- and E-selective Hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different.

  • Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E‑Selective Hydroarylation of Terminal Alkynes
    2018
    Co-Authors: Megan K. Armstrong, Madison B Goodstein, Gojko Lalic
    Abstract:

    A diastereodivergent Hydroarylation of terminal alkynes is accomplished using tandem catalysis. The Hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The Hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective Hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semireduction. The E-selective Hydroarylation involves an additional catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the Hydroarylation. Our studies also show that, although the Z- and E-selective Hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different

Erik V. Van Der Eycken - One of the best experts on this subject based on the ideXlab platform.