Metal‐Free 1,5‐Regioselective Azide–Alkyne [3+2]‐Cycloaddition

Kloß, Florian; Köhn, Uwe; Jahn, Burkhard O.; Hager, Martin D.; Görls, Helmar; Schubert, Ulrich S.

doi:10.1002/asia.201100404

Cited by 42 publications

(24 citation statements)

References 74 publications

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“…Moreover, the 1,3-dipolar cycloaddition of perfluorinated aryl azides with enamines and strained dipolarophiles has been studied (Xie et al, 2015). Additionally, non-catalytic Huisgen (3 + 2) cycloaddition of perfluorophenylazide with ethyl propiolate and a one-pot tandem Sonogashira cross-coupling/CuAAC reaction were studied (Kloss et al. 2011).…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis, crystal structure and Hirshfeld surface analysis of (4-methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-4-yl]methanone

Pokhodylo¹,

Slyvka²,

Goreshnik³

et al. 2021

Acta Cryst E

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The title compound, C17H7F8N3O, was obtained via the reaction of 1-azido-2,3,4,5,6-pentafluorobenzene with 4,4,4-trifluoro-1-(p-tolyl)butane-1,3-dione using triethylamine as a base catalyst and solvent. The dihedral angles between the pentafluorophenyl (A), triazole (B) and p-tolyl (C) rings are A/B = 62.3 (2), B/C = 43.9 (3) and A/C = 19.1 (3)°. In the crystal, the molecules are linked by C—H...F and C—H...O hydrogen bonds as well as by aromatic π–π stacking interactions into a three-dimensional network. To further analyse the intermolecular interactions, a Hirshfeld surface analysis was performed.

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Section: Chemical Contextmentioning

confidence: 99%

Synthesis, crystal structure and Hirshfeld surface analysis of (4-methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-4-yl]methanone

Pokhodylo¹,

Slyvka²,

Goreshnik³

et al. 2021

Acta Cryst E

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“…The regioselectivity of the [3+2] cycloaddition of azides to alkynes can be altered to the 1,5-disubstituted 1,2,3-triazoles by using other transition metalbased catalysts such as ruthenium [43,44], palladium [45], or by the use of silyl acetylene or a bromomagnesium acetylide [46,47]. In a recent approach, the synthesis of 1,5-disubstituted 1,2,3-triazoles was achieved from 1,3,4-trisubstituted 1,2,3-triazolium salts with a 3,4-dimethoxybenzyl protecting group at position 1, which was later removed by means of ammonium nitrate or ceric ammonium nitrate (CAN) [48].…”

Section: Synthesis Of 123-triazolium Ionic Liquidsmentioning

confidence: 99%

Chemistry of 1,2,3-Triazolium Salts

Yacob¹,

Liebscher²

2014

Topics in Heterocyclic Chemistry

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1,2,3-Triazolium salts have been known for a long time. However, their potential as ionic liquids and catalysts was recognized only quite recently. 1,2,3-Triazolium ionic liquids can serve as solvent, as catalyst, as hosts in anion recognition and as components of molecular machines. The major trends in application involve tethering catalytically active species such as (S)-proline with triazolium ionic liquids and the use as anion recognizing organocatalysts. Such catalysts are interesting not only due to their recyclability but also because of their outstanding tuneable properties. They can have wide liquid range, thermal stability, tuneable polarity, low flammability, tuneable solubility and low vapour pressure along with ease of separation. The syntheses of 1,2,3-triazolium salts are mainly based on the copper catalysed azide-alkyne cycloaddition (CuAAC) as the most famous click reaction, and subsequent N-alkylation of the resulting 1,2,3-triazoles. This synthetic route has the advantage of having four structural units, i.e. the alkyne, the azide, the alkylating agent and the counter anion that can be manipulated in order to tune the properties of the resulting ionic liquid. Unlike the imidazolium ionic liquids 1,2,3-triazolium salts do not have an acidic proton at position 2, which could make them inappropriate for reactions under basic conditions. The low acidity of 1,2,3triazolium salts in position 4 is exploited in the formation of 1,2,3-triazol-4-ylidene metal complexes with marked catalytic properties.

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“…The method of building up these structures is underlain by the "click-reaction" leading to the formation of the corresponding Cu(I)-triazolide intermediate 124 . -cycloaddition of substituted aromatic azides to trimethylsilylacetylenes in water affording regioisomeric 1,2,3-triazoles, in particular, those containing a perfl uoroaryl substituent at endocyclic atoms of the heterocycle 125, 126 [ 111 ]. Recently, a number of chiral phosphoramidite ligands 127 containing 1,2,3-triazole ring at the 3,3′-positions of the binol scaffold were synthesized by McErlean et al [ 112 ].…”

Section: 23-triazolesmentioning

confidence: 99%