β‐Enaminone Synthesis from 1,3‐Dicarbonyl Compounds and Aliphatic and Aromatic Amines Catalyzed by Iron Complexes of Fused Bicyclic Imidazo[1,5‐<i>a</i>]pyridine Derived N‐Heterocyclic Carbenes

Prakasham, A. P.; Gangwar, Manoj Kumar; Ghosh, Prasenjit

doi:10.1002/ejic.201800906

Cited by 15 publications

(3 citation statements)

References 75 publications

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“…The calculated geometries of 1b and 3a show excellent agreement with the corresponding solid-state structures of complexes 1 and 3 obtained by X-ray diffraction. Since the difference in the main thermodynamic characteristics (Δ E , Δ H 298 , and Δ G 298 ) between these horizontal and eclipsed isomers (Table S2) does not exceed 1.6 kcal mol –1 , it is not surprising that either one or both conformations have been observed by single-crystal X-ray diffraction in parent [Cp(CO) 2 M(NHC)] n + (M = Mn, n = 0; ,, M = Fe, n = 1) complexes bearing N-aryl-substituted NHC ligands, and these rotamers are likely to be in fast exchange in solution.…”

Section: Resultsmentioning

confidence: 99%

Experimental and Theoretical Insights into the Electronic Properties of Anionic N-Heterocyclic Dicarbenes through the Rational Synthesis of Their Transition Metal Complexes

et al. 2021

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The lithiation of the NHC ligand backbone in Cp(CO)2Mn(IMes) followed by transmetallation on the C4 carbenic position with Cp(CO)2FeI led to the heterobimetallic complex Cp(CO)2Mn(μ-dIMes)Fe(CO)2Cp bearing the anionic ditopic imidazol-2,4-diylidene dIMes ligand. Subsequent treatment of the later with TfOH induced a selective decoordination of the [Cp(CO)2Mn] fragment to form the cationic abnormal NHC complex [Cp(CO)2Fe(aIMes)](OTf), which was further derivatized into the bis(iron) dIMes complex [Cp(CO)2Fe(μ-dIMes)Fe(CO)2Cp](OTf) by reaction with tAmOK and Cp(CO)2FeI. The effect of the metallation at the C4 or C2 positions of imidazole ring on the electronic donation properties of the associated C2 and C4 carbenic centers in dIMes ligand was quantified through systematic experimental and theoretical studies of IMes, aIMes and dIMes complexes. The evaluation of the catalytic activity of the series of cationic Fe(II) complexes based on IMes, aIMes, and dIMes ligands in a benchmark ketone hydrosilylation showed the superiority of the bimetallic derivative.

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Section: Resultsmentioning

confidence: 99%

Experimental and Theoretical Insights into the Electronic Properties of Anionic N-Heterocyclic Dicarbenes through the Rational Synthesis of Their Transition Metal Complexes

et al. 2021

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“…Iron and cobalt complexes based on imidazopyridine have been synthesized and structurally characterized [ 149 , 150 , 151 , 152 , 153 ]; initial findings suggest the spontaneous resolution of enantiomers during crystallization, indicative of a rare p-donor/p-acceptor chiral recognition mechanism [ 154 ].…”

Section: Studies and Applications Of Imidazopyridine Derivativesmentioning

confidence: 99%

Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications

Volpi,

Laurenti,

Rabezzana

2024

Molecules

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In recent years, there has been increasing attention focused on various products belonging to the imidazopyridine family; this class of heterocyclic compounds shows unique chemical structure, versatile optical properties, and diverse biological attributes. The broad family of imidazopyridines encompasses different heterocycles, each with its own specific properties and distinct characteristics, making all of them promising for various application fields. In general, this useful category of aromatic heterocycles holds significant promise across various research domains, spanning from material science to pharmaceuticals. The various cores belonging to the imidazopyridine family exhibit unique properties, such as serving as emitters in imaging, ligands for transition metals, showing reversible electrochemical properties, and demonstrating biological activity. Recently, numerous noteworthy advancements have emerged in different technological fields, including optoelectronic devices, sensors, energy conversion, medical applications, and shining emitters for imaging and microscopy. This review intends to provide a state-of-the-art overview of this framework from 1955 to the present day, unveiling different aspects of various applications. This extensive literature survey may guide chemists and researchers in the quest for novel imidazopyridine compounds with enhanced properties and efficiency in different uses.

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“…With our interest in exploring the potentials of the transition metal complexes of the heteroatom stabilized cyclic and acyclic singlet carbene ligands in homogeneous catalysis − and in biomedical applications, we study different singlet-carbene ligand classes covering the cyclic normal N-heterocyclic carbenes, abnormal mesoionic carbenes , the acyclic diaminocarbenes , and the fused-cyclic ones of the imidazole, benzimidazole, triazole, ,, oxazolidine, bioxazoline, and triazolooxazine architectures. The mesoionic (MIC) carbenes, featuring less heteroatom stabilization than the more ubiquitous normal N-heterocyclic carbenes, come with specific donors and reactivity properties but surprisingly remain less explored .…”

Section: Introductionmentioning

confidence: 99%

Accessing Heteroannular Benzoxazole and Benzimidazole Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived from a Phenothiazine Moiety

Dey

Ghosh

2023

ACS Omega

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The coupling of aryl and aliphatic azides with isocyanides yielding carbodiimides (8–17) were efficiently catalyzed by well-defined structurally characterized trans-(MIC)PdI2(L) [MIC = 1-CH2Ph-3-Me-4-(CH2N(C6H4)2S)-1,2,3-triazol-5-ylidene, L = NC5H5 (4), MesNC (5)], trans-(MIC)2PdI2 (6), and cis-(MIC)Pd(PPh3)I2 (7) type palladium complexes, which incidentally mark the first instances of the use of mesoionic singlet palladium carbene complexes for the said application. As observed from the product yields, the catalytic activity varied in the order 4 > 5 ∼ 6 > 7 for these complexes. A detailed mechanistic studies indicated that the catalysis proceeded via a palladium(0) (4a–7 a) species. Using a representative palladium precatalyst (4), the azide–isocyanide coupling was successfully extended to synthesizing two different bioactive heteroannular benzoxazole (18–22) and benzimidazole (23–27) derivatives, thereby broadening the scope of the catalytic application.

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β‐Enaminone Synthesis from 1,3‐Dicarbonyl Compounds and Aliphatic and Aromatic Amines Catalyzed by Iron Complexes of Fused Bicyclic Imidazo[1,5‐a]pyridine Derived N‐Heterocyclic Carbenes

Cited by 15 publications

References 75 publications

Experimental and Theoretical Insights into the Electronic Properties of Anionic N-Heterocyclic Dicarbenes through the Rational Synthesis of Their Transition Metal Complexes

Experimental and Theoretical Insights into the Electronic Properties of Anionic N-Heterocyclic Dicarbenes through the Rational Synthesis of Their Transition Metal Complexes

Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications

Accessing Heteroannular Benzoxazole and Benzimidazole Scaffolds via Carbodiimides Using Azide–Isocyanide Cross-Coupling as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived from a Phenothiazine Moiety

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