Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes

Aizpurua, J. M.; Sagartzazu‐Aizpurua, Maialen; Monasterio, Zaira; Azcune, Itxaso; Mendicute, Claudio; Miranda, José I.; García-Lecina, Eva; Altube, A.; Fratila, Raluca M.

doi:10.1021/ol3004657

Cited by 30 publications

(10 citation statements)

References 28 publications

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“…123 Bis(triazolylidene) NHC-275 shows three stretches in the IR spectrum, corresponding to two TEPs. 187 Caffeine-derived NHC-276 has also been reported. 107 Bertrand and have reported the syntheses and characterisation of bis(diisopropylamino)cyclopropenylidene C-2 and bent allenes C-1, C-3 and C-4 (Fig.…”

Section: From [Rhcl(co) 2 (Nhc)] Complexesmentioning

confidence: 97%

Quantifying and understanding the electronic properties of N-heterocyclic carbenes

2013

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The use of N-heterocyclic carbenes (NHCs) in chemistry has developed rapidly over the past twenty years. These interesting compounds are predominantly employed in organometallic chemistry as ligands for various metal centres, and as organocatalysts able to mediate an exciting range of reactions. However, the sheer number of NHCs known in the literature can make the appropriate choice of NHC for a given application difficult. A number of metrics have been explored that allow the electronic properties of NHCs to be quantified and compared. In this review, we discuss these various metrics and what they can teach about the electronic properties of NHCs. Data for approximately three hundred NHCs are presented, obtained from a detailed survey of the literature.

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Section: From [Rhcl(co) 2 (Nhc)] Complexesmentioning

confidence: 97%

Quantifying and understanding the electronic properties of N-heterocyclic carbenes

2013

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“…537,543,548 On the other hand, cyclometalation of 74 involving the central carbanionic donor as known for the imidazol-2-ylidene-analog 570 has not been reported yet to the best of our knowledge. Alternatively, the bis(triazolylidene) ligands can serve as bridging ligands and homobimetallic complexes of 71 in axial chirality) 571 as well as of 74 555,557,561 and even heterobimetallic complexes of 74 561 have been reported. Furthermore, heterobimetallic complexes of dicarbenes composed of imidazol-2-ylidene and triazolylidene were reported, 562 and unsymmetrically substituted bis(triazolylidene) ligands 71 are available.…”

Section: 23-triazolylidenes As Mesoionic Carbene Ligandsmentioning

confidence: 99%

“…Furthermore, heterobimetallic complexes of dicarbenes composed of imidazol-2-ylidene and triazolylidene were reported, 562 and unsymmetrically substituted bis(triazolylidene) ligands 71 are available. [571][572][573] 5.4.3. Reactivity of 1,2,3-triazolylidenes.…”

Section: 23-triazolylidenes As Mesoionic Carbene Ligandsmentioning

confidence: 99%

Beyond click chemistry – supramolecular interactions of 1,2,3-triazoles

2014

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The research on 1,2,3-triazoles has been lively and ever-growing since its stimulation by the advent of click chemistry. The attractiveness of 1H-1,2,3-triazoles and their derivatives originates from their unique combination of facile accessibility via click chemistry and truly diverse supramolecular interactions, which enabled myriads of applications in supramolecular and coordination chemistry. The nitrogen-rich triazole features a highly polarized carbon atom allowing the complexation of anions by hydrogen and halogen bonding or, in the case of the triazolium salts, via charge-assisted hydrogen and halogen bonds. On the other hand, the triazole offers several N-coordination modes including coordination via anionic and cationic nitrogen donors of triazolate and triazolium ions, respectively. After CH-deprotonation of the triazole and the triazolium, powerful carbanionic and mesoionic carbene donors, respectively, are available. The latter coordination mode even features non-innocent ligand behavior. Moreover, these supramolecular interactions can be combined, e.g., in ion-pair recognition, preorganization by intramolecular hydrogen bond donation and acceptance, and in bimetallic complexes. Ultimately, by clicking two building blocks into place, the triazole emerges as a most versatile functional unit allowing very successful applications, e.g., in anion recognition, catalysis, and photochemistry, thus going far beyond the original purpose of click chemistry. It is the intention of this review to provide a detailed analysis of the various supramolecular interactions of triazoles in comparison to established functional units, which may serve as guidelines for further applications.

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“…With the striking development of the copper‐catalyzed azide‐alkyne cycloaddition (CuAAC, the most developed example of click chemistry reactions),7 1,2,3‐triazole groups have been increasingly popular linking units in a broad variety of molecular and macromolecular structures 8–13. Recently, several 1,4‐disubstituted‐1,2,3‐triazolium ionic liquids have been developed,14–20 and their potential as efficient reaction media,21 anion‐templated formation of rotaxanes,22 receptors for anion recognition,23 stereoselective organocatalysts,24 ligands for ruthenium‐catalyzed olefin metathesis,25 as well as precursors of N ‐heterocyclic carbene ligands for palladium‐catalyzed Suzuki coupling have been established 26. The scope of this communication is to demonstrate the unprecedented synthesis of 1,2,3‐triazolium‐based PILs and their potential as new ionic conducting materials.…”

Section: Introductionmentioning

confidence: 99%

Main‐chain 1,2,3‐triazolium‐based poly(ionic liquid)s issued from AB + AB click chemistry polyaddition

Dimitrov-Raytchev

Beghdadi

Serghei

et al. 2012

J. Polym. Sci. A Polym. Chem.

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present the synthesis of four new chiral monomers and polymers based on menthol. Their chemical structures, phase behavior, and thermal stability are characterized by FT-IR, NMR, DSC, POM, XRD, and TGA. By inserting a flexible spacer between the mesogenic core and the terminal menthyl groups, the target monomers and polymers can form the SmC*, cholesteric, and SmA phases. By increasing the mesogenic core rigidity, the corresponding T m , T g , and T i increased. In addition, increasing the spacer length decreased the T m and T g , while T i increased. POLYMER NANOSPHERES Polyacetylenes are formed upon irradiation with gamma rays of ortho-substituted aryl alkynes 2-RC 6 H 4 CBCH (R = CF 3 , OMe, Me) in methanol solutions. An osmosis driven manipulation allows the soluble polymers to aggregate in the form of nanospheres, as well as hollow nanospheres, of different dimensions. The finding and development of this transition metal-free activation process of terminal alkynes come from the collaboration of three research groups with authors Mauro Bassetti, Ilaria Fratoddi, Laura Lilla, Chiara Pasquini, Maria Vittoria Russo, and Ornella Ursini, as presented on page 5097. The SEM image in the picture highlights the shape and size of the nanoparticles obtained via the osmosis-based methodology for one of these polymers (R = CF 3).

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Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes

Cited by 30 publications

References 28 publications

Quantifying and understanding the electronic properties of N-heterocyclic carbenes

Quantifying and understanding the electronic properties of N-heterocyclic carbenes

Beyond click chemistry – supramolecular interactions of 1,2,3-triazoles

Main‐chain 1,2,3‐triazolium‐based poly(ionic liquid)s issued from AB + AB click chemistry polyaddition

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