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Ruthenium‐Catalyzed Cycloaddition of 1,6‐Diynes and Nitriles under Mild Conditions: Role of the Coordinating Group of Nitriles
Author(s) -
Yamamoto Yoshihiko,
Kinpara Keisuke,
Ogawa Ryuji,
Nishiyama Hisao,
Itoh Kenji
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600176
Subject(s) - nitrile , cycloaddition , chemistry , lone pair , catalysis , ruthenium , medicinal chemistry , heteroatom , group (periodic table) , bicyclic molecule , triple bond , organic chemistry , double bond , ring (chemistry) , molecule
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 CC triple bond or heteroatom substituents, such as methoxy and methylthio groups, proved to act as the coordinating groups, whereas CC or CO 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.