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Coordinatively Unsaturated Ruthenium Complexes As Efficient Alkyne-Azide Cycloaddition Catalysts

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((PPr3)-Pr-i)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((PPr3)-Pr-i)(eta(2)-HCCPh)Cl was observed and characterized by H-1, C-13, and P-31 NMR at temperatures between 273 and 213 K. A rare example of N,N-kappa(2)-phosphazide complex, Cp*Ru(kappa(2)-(Pr3PN3Bn)-Pr-i)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

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)

© Organometallics, 2012, vol. 31, núm. 2, p. 756-767

American Chemical Society

Author: Lamberti, Marina
Fortman, George C.
Poater Teixidor, Albert
Broggi, Julie
Slawin, Alexandra M. Z.
Cavallo, Luigi
Nolan, Steven P.
Date: 2012
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((PPr3)-Pr-i)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((PPr3)-Pr-i)(eta(2)-HCCPh)Cl was observed and characterized by H-1, C-13, and P-31 NMR at temperatures between 273 and 213 K. A rare example of N,N-kappa(2)-phosphazide complex, Cp*Ru(kappa(2)-(Pr3PN3Bn)-Pr-i)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
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)
Format: application/pdf
ISSN: 0276-7333 (versió paper)
1520-6041 (versió electrònica)
Document access: http://hdl.handle.net/10256/8659
Language: eng
Publisher: American Chemical Society
Collection: MICINN/PN 2012-2015/RYC-2009-05226
Reproducció digital del document publicat a: http://dx.doi.org/10.1021/om2012425
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/293900
Is part of: © Organometallics, 2012, vol. 31, núm. 2, p. 756-767
Rights: Tots els drets reservats
Subject: Ruteni -- Compostos
Ruthenium compounds
Catalitzadors
Catalysts
Metàtesi (Química)
Metathesis (Chemistry)
Ciclització (Química)
Ring formation (Chemistry)
Title: Coordinatively Unsaturated Ruthenium Complexes As Efficient Alkyne-Azide Cycloaddition Catalysts
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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