Coordinatively unsaturated ruthenium complexes as efficient alkyne-azide cycloaddition catalysts

Marina Lamberti, George C. Fortman, Albert Poater, Julie Broggi, Alexandra M. Z. Slawin, Luigi Cavallo, Steven P. Nolan

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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 azide−alkyne cycloaddition reactions that afford the 1,2,3- triazole products. The scope of the Cp*Ru(PiPr3)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)(η2-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.
Original languageEnglish
Pages (from-to)756-767
Number of pages12
JournalOrganometallics
Volume31
Issue number2
Early online date10 Jan 2012
DOIs
Publication statusPublished - 23 Jan 2012

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