期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 12, 期 21, 页码 5618-5631出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200600176
关键词
alkynes; cycloaddition; nitriles; pyridine; ruthenium catalysis
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 nitrites 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 C triple bond or heteroatom substituents, such as methoxy and methylthio groups, proved to act as the coordinating groups, whereas C=C or C=0 double bonds and amino groups failed to promote cycloaddition. This suggests that coordinating groups with multiple it-bonds or lone pairs are essential for the nitrile components.
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