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Published on: September 21, 2019
Synthesis of Multisubstituted Azatriphenylenes by Iridium-Catalyzed [2 + 2 + 2] Cycloaddition of Biaryl-Linked Diynes
Ryo Takeuchi1, Shunsuke Fujisawa1, Yuzo Yoshida1
1Department of Chemistry and Biological Science, Aoyama Gakuin University , 5-10-1 Fuchinobe, Chuo, Sagamihara, Kanagawa 252-5258, Japan.
Abstract:
A convenient synthesis of multisubstituted azatriphenylenes is reported. [Ir(cod)Cl]2/diphosphine is an efficient catalyst for the [2 + 2 + 2] cycloaddition of biaryl-linked diynes with nitriles to give multisubstituted azatriphenylenes in high yields. Aromatic, heteroaromatic, aliphatic, and functionalized nitriles could be used for the reaction.
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In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
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The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
SN2 Reaction: Transition State
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...

