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    Coordinatively unsaturated ruthenium complexes as efficient alkyneazide cycloaddition catalysts

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    Type
    Article
    Authors
    Lamberti, Marina
    Fortman, George C.
    Poater, Albert cc
    Broggi, Julie
    Slawin, Alexandra M. Z.
    Cavallo, Luigi cc
    Nolan, Steven P. cc
    KAUST Department
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2012-01-10
    Online Publication Date
    2012-01-10
    Print Publication Date
    2012-01-23
    Permanent link to this record
    http://hdl.handle.net/10754/562064
    
    Metadata
    Show full item record
    Abstract
    The performance of 16-electron ruthenium complexes with the general formula Cp*Ru(L)X (in which L = phosphine or N-heterocyclic carbene ligand; X = Cl or OCH2CF3) was explored in azidealkyne cycloaddition reactions that afford the 1,2,3- triazole products. The scope of the Cp*Ru(PiPr 3)Cl precatalyst was investigated for terminal alkynes leading to new 1,5-disubstituted 1,2,3-triazoles in high yields. Mechanistic studies were conducted and revealed a number of proposed intermediates. Cp*Ru- (PiPr3)(2-HCCPh)Cl was observed and characterized by 1H, 13C, and 31P NMR at temperatures between 273 and 213 K. A rare example of N,N-κ2-phosphazide complex, Cp*Ru(κ2- iPr3PN3Bn)Cl, was fully characterized, and a single-crystal X-ray diffraction structure was obtained. DFT calculations describe a complete map of the catalytic reactivity with phenylacetylene and/or benzylazide. © 2012 American Chemical Society.
    Citation
    Lamberti, M., Fortman, G. C., Poater, A., Broggi, J., Slawin, A. M. Z., Cavallo, L., & Nolan, S. P. (2012). Coordinatively Unsaturated Ruthenium Complexes As Efficient Alkyne–Azide Cycloaddition Catalysts. Organometallics, 31(2), 756–767. doi:10.1021/om2012425
    Sponsors
    S.P.N. would like to thank the ERC (Advanced Researcher Award FUNCAT) for financial support. A.P. thanks the Spanish MICINN for a Ramon y Cajal contract (ref RYC-2009-05226) and the European Commission for a Career Integration Grant (CIG09-GA-2011-293900). L.C. and A.P. thank the HPC team of Enea (www.enea.it) for using the ENEA-GRID and the HPC facilities CRESCO (www.cresco.enea.it) in Portici, Italy. M.L. acknowledges Salerno Province and the University of Salerno for supporting her stay at the University of St Andrews (International Mobility Scholarship 2009). S.P.N. is a Royal Society Wolfson Research Merit Award holder.
    Publisher
    American Chemical Society (ACS)
    Journal
    Organometallics
    DOI
    10.1021/om2012425
    Relations
    Is Supplemented By:
    • [Dataset]
      Lamberti, M., Fortman, G. C., Poater, A., Broggi, J., Slawin, A. M. Z., Cavallo, L., & Nolan, S. P. (2013). CCDC 820903: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccwk6rc. DOI: 10.5517/ccwk6rc HANDLE: 10754/624639
    ae974a485f413a2113503eed53cd6c53
    10.1021/om2012425
    Scopus Count
    Collections
    Articles; Biological and Environmental Science and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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