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Ruthenium-Catalyzed Cycloaddition of 1,6-Diynes and Nitriles under Mild Conditions: Role of the Coordinating Group of Nitriles

Authors

  • Yoshihiko Yamamoto Prof. Dr.,

    1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464–8603, Japan, Fax: (+81) 52-789-3209
    2. Current address: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okatyama, Meguro-ku, Tokyo 152–8552, Japan
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  • Keisuke Kinpara,

    1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464–8603, Japan, Fax: (+81) 52-789-3209
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  • Ryuji Ogawa,

    1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464–8603, Japan, Fax: (+81) 52-789-3209
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  • Hisao Nishiyama Prof. Dr.,

    1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464–8603, Japan, Fax: (+81) 52-789-3209
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  • Kenji Itoh Prof. Dr.

    1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464–8603, Japan, Fax: (+81) 52-789-3209
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Abstract

In the presence of a catalytic amount of [Cp*RuCl(cod)] (Cp*=pentamethylcyclopentadienyl, cod=1,5-cyclooctadiene), 1,6-diynes were allowed to react chemo- and regioselectively with nitriles bearing a coordinating group, such as dicyanides or α-halonitriles, at ambient temperature to afford bicyclic pyridines. Careful screening of nitrile components revealed that a C[TRIPLE BOND]C triple bond or heteroatom substituents, such as methoxy and methylthio groups, proved to act as the coordinating groups, whereas C[DOUBLE BOND]C or C[DOUBLE BOND]O double bonds and amino groups failed to promote cycloaddition. This suggests that coordinating groups with multiple π-bonds or lone pairs are essential for the nitrile components.

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