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  • Title: Ruthenium-catalyzed cycloaddition of 1,6-diynes and nitriles under mild conditions: role of the coordinating group of nitriles.
    Author: Yamamoto Y, Kinpara K, Ogawa R, Nishiyama H, Itoh K.
    Journal: Chemistry; 2006 Jul 17; 12(21):5618-31. PubMed ID: 16755621.
    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 alpha-halonitriles, at ambient temperature to afford bicyclic pyridines. Careful screening of nitrile components revealed that a C[triple chemical bond]C triple bond or heteroatom substituents, such as methoxy and methylthio groups, proved to act as the coordinating groups, whereas C==C or C==O double bonds and amino groups failed to promote cycloaddition. This suggests that coordinating groups with multiple pi-bonds or lone pairs are essential for the nitrile components.
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