Ruthenium-Catalyzed Cycloaddition of 1,6-Diynes and Nitriles under Mild Conditions: Role of the Coordinating Group of Nitriles
- 7 July 2006
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 12 (21), 5618-5631
- https://doi.org/10.1002/chem.200600176
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 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.Keywords
This publication has 74 references indexed in Scilit:
- Bispyridylamides?coordination chemistry and applications in catalytic reactionsCoordination Chemistry Reviews, 2005
- Chiral pyridine N-oxides: useful ligands for asymmetric catalysisTetrahedron: Asymmetry, 2004
- Construction of Pyridine Rings by Metal-Mediated [2 + 2 + 2] CycloadditionChemical Reviews, 2003
- Chiral 2,2‘-Bipyridines, 1,10-Phenanthrolines, and 2,2‘:6‘,2‘ ‘-Terpyridines: Syntheses and Applications in Asymmetric Homogeneous CatalysisChemical Reviews, 2002
- Cyclomerization of AlkynesPublished by Wiley ,1998
- Catalytic co-cyclisation of α,ω-cyanoalkynes with alkynes: a versatile chemo- and regio-selective synthesis of 2,3-substituted 5,6,7,8-tetrahydroquinolines and other cycloalka[1,2-b]pyridinesJournal of the Chemical Society, Chemical Communications, 1982
- Cobalt‐katalysierte einstufige Synthese von anellierten PyridinenAngewandte Chemie, 1977
- A Cobalt‐Catalyzed One‐Step Synthesis of Annelated PyridinesAngewandte Chemie International Edition in English, 1977
- Novel synthesis of heterocyclic compounds from acetylenesJournal of the Chemical Society, Chemical Communications, 1973
- CXIX.—The formation and stability of spiro-compounds. Part I. spiro-Compounds from cyclohexaneJournal of the Chemical Society, Transactions, 1915