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

doi:10.1021/om2012425

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	756-767
Number of pages	12
Journal	Organometallics
Volume	31
Issue number	2
Early online date	10 Jan 2012
DOIs	https://doi.org/10.1021/om2012425
Publication status	Published - 23 Jan 2012

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10.1021/om2012425

Lambertietal2012OrganometallicsRuthenium
(c) 2012 American Chemical Society
Final published version, 2.43 MB

FUNCAT: EU FP7 ERC Advanced Grant - FUNCAT - Fundamental Studies in Organometallic Chemistry and Homogeneous Catalysis
Nolan, S. (PI)
European Research Council
1/01/09 → 31/12/14
Project: Standard

Cite this

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title = "Coordinatively unsaturated ruthenium complexes as efficient alkyne-azide cycloaddition catalysts",

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.",

author = "Marina Lamberti and Fortman, {George C.} and Albert Poater and Julie Broggi and Slawin, {Alexandra M. Z.} and Luigi Cavallo and Nolan, {Steven P.}",

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T1 - Coordinatively unsaturated ruthenium complexes as efficient alkyne-azide cycloaddition catalysts

AU - Lamberti, Marina

AU - Fortman, George C.

AU - Poater, Albert

AU - Broggi, Julie

AU - Slawin, Alexandra M. Z.

AU - Cavallo, Luigi

AU - Nolan, Steven P.

PY - 2012/1/23

Y1 - 2012/1/23

N2 - 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.

AB - 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.

U2 - 10.1021/om2012425

DO - 10.1021/om2012425

M3 - Article

SN - 0276-7333

VL - 31

SP - 756

EP - 767

JO - Organometallics

JF - Organometallics

IS - 2

ER -

Coordinatively unsaturated ruthenium complexes as efficient alkyne-azide cycloaddition catalysts

Abstract

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Projects

FUNCAT: EU FP7 ERC Advanced Grant - FUNCAT - Fundamental Studies in Organometallic Chemistry and Homogeneous Catalysis

Cite this