Reaction mechanism of ruthenium-catalyzed azide–alkyne cycloaddition reaction: A DFT study

Boz, Esra; Tüzün, Nurcan Ş.

doi:10.1016/j.jorganchem.2012.11.011

Cited by 38 publications

(17 citation statements)

References 37 publications

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“…These authors showed also that the formation of the 1,5-triazole is highly disfavored. This is in line with Boz and Tüzün's theoretical work (see above) that indicated the importance of the electronic and steric effects for the regioselectivity, both thermodynamic and kinetic parameters playing a crucial role in the reactions [41]. Lo's group presented the first case of ruthenium azido complexes catalyzing the cycloaddition reaction of terminal alkynes with alkyl azides [90,91].…”

Section: The Ruaac Reactionssupporting

confidence: 71%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

293

162

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Highlights-The review is focused on the mechanistic aspects and recent trends (since 2012) of the metal-catalyzed azide-alkyne cycloaddition (MAAC) so-called "click" reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.-These MAAC reactions are by far the most common click reactions relevant to the "green chemistry" concept.-Mechanistic investigations are essential to reaction improvements and subsequent applications, and indeed as shown in this review the proposed mechanisms have been multiple during the last decade based on theoretical computations and experimental search of intermediates.-New trends are also presented here often representing both exciting approaches for various applications and new challenges for further mechanistic investigations.

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Section: The Ruaac Reactionssupporting

confidence: 71%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

293

162

View full text Add to dashboard Cite

show abstract

“…The reaction was later revisited in detail by using alternative substrates including Cp * , which confirmed the reaction paths determined earlier, but further explained the effect of different substituents on the reaction rate and the product ratio of 1,4-and 1,5-regioisomers. 58 Based on the results, Boren et al…”

Section: Mechanistic and Theoretical Studiesmentioning

confidence: 99%

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

et al. 2016

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The ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) affords 1,5-disubstituted 1,2,3-triazoles in one step and complements the more established copper-catalyzed reaction providing the 1,4-isomer. The RuAAC reaction has quickly found its way into the organic chemistry toolbox and found applications in many different areas, such as medicinal chemistry, polymer synthesis, organocatalysis, supramolecular chemistry and the construction of 2 electronic devices. This review discusses the mechanism, scope and applications of the RuAAC reaction, covering the literature during the last 10 years. CONTENTS

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“…[12g, 465,471] Interesting transformations at Ru II finally ending up in organic 1,2,3-triazoles and a cyanoruthenium species CpRu(CN)(PPh 3 ) 2 play out in the reactions of the cyclopropenylruthenium complexes CpRu{-C=C(Ph)CHR}(PPh 3 ) 2 (93) (R = CH=CH 2 , CH=CH-CO 2 Me) with two moles of TMSN 3 . [361,472] The reaction of the cyano-substituted cyclopropenyl complex 93 (R = CN) with SiMe 3 N 3 took a different route affording the tetrazolato complex [Ru]{N 4 CCH(Ph)CH 2 CN} (49) (see section 1.8.).…”

Section: Reactions Of Main Group Element Azides With Alkynesmentioning

confidence: 99%

Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

Fehlhammer

Beck

2015

Zeitschrift anorg allge chemie

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Abstract. In whatever state of bonding -whether covalent to an organic residue or a heteroatom, or polar to ionic in contact with a metal -the azide moiety N 3 is characterized by its high potential of reactivity which essentially manifests itself in two basic processes: the elimination of dinitrogen and the entry into 1,3-dipolar cycloadditions with suitable dipolarophiles, the latter of which clearly predominates the chemistry of azide, also that of its metal compounds. In a preceding review entitled "Part I -Metal Azides: Overview, General Trends and Recent Developments" which was meant to lay the foundations for the present paper, these and other reactions have already been touched upon. The present review -Part II -now focusses in great detail on the formation of five-membered heterocyclestetrazol(at)es, triazol(at)es, triazolin(at)es, thiatriazol(at)es, etc. as well as various consecutive products -from azide and nitriles, isocyanides, alkynes, alkenes and heteroallenes (CS 2 , RN=C=S) in the ligand sphere of the metal. Generally, these [3+2]-cycloadditions are found to CONTENTS

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Reaction mechanism of ruthenium-catalyzed azide–alkyne cycloaddition reaction: A DFT study

Cited by 38 publications

References 37 publications

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

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Reaction mechanism of ruthenium-catalyzed azide–alkyne cycloaddition reaction: A DFT study

Cited by 38 publications

References 37 publications

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

Azide Chemistry – An Inorganic Perspective, Part II[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

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Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems