Synthesis, structure and electrochemistry of new diferrocenyl pyridine derivatives

Wang, Yaqi; Han, Limin; Suo, Quan‐Ling; Zhu, Na; Hao, Jianmin; Xie, Rongrong

doi:10.1016/j.poly.2013.02.043

Cited by 9 publications

(2 citation statements)

References 32 publications

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“…These electronic interaction properties can be associated with the atomic outer boundaries, ionization degree, and hybridization structure factors [16][17][18] . However, when diferrocenyl derivatives containing aromatic rings spacers, the charge transfers are in uenced by various complex factors, including metalmetal center distance 19 , position of substituent 20 , center ring geometric properties 21 , topology 22 and aromatic properties 23,24 , which in uencing factor is the primary factor of intramolecular electron transfer is still an academic debate. In order to further explore this problem, more and more researchers are engaged in numerous heterocycle spacers' studies, especially the ve-membered aromatic heterocycle spacers 25,26 , because these spacers involves π-conjugate structure and heteroatom, which can provide changing chemical structure for studying.…”

Section: Introductionmentioning

confidence: 99%

The Intramolecular Electronic Interaction Regulated by Five-membered Heterocycle Spacer

Han

Wang

2021

Preprint

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The spacer in diferrocenyl derivatives has significant effects on intramolecular electronic interaction properties. In this work, nine diferrocenyl five-membered heterocyclic molecules are synthesized as models to investigate the effect of intramolecular electron-transfer properties systematically, including 2,5-diferrocenyl-1-phenyl-pyrrole (1), 2,5-diferrocenylfuran (2), 2,5-diferrocenylthiophene (3), 2,5-diferrocenyl-1H-imidazole (4), 2,5-diferrocenyloxazole (5), 2,5-diferrocenylthiazole (6), 2,5-diferrocenyl-1,3,4-triazole (7), 2,5-diferrocenyl-1,3,4-oxadiazole (8) and 2,5-diferrocenyl-1,3,4-thiadiazole (9). The molecules were prepared in cyclization reaction and characterized by Elemental analysis, FT-IR, MS and NMR. Moreover, the molecular structures of 2,5-diferrocenylthiazole and 2,5-diferrocenyl-1,3,4-oxadiazole were determined by the single crystal X-ray diffraction. The intramolecular electronic interactions were investigated through cyclic voltammetry in combination with density functional theory (DFT) calculations. The results revealed that the electronic interaction decreased with the increase of heteroatoms in central heterocycle spacer, and the electron-transfer property could be regulated by regulate central heterocycle spacer species.

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Section: Introductionmentioning

confidence: 99%

The Intramolecular Electronic Interaction Regulated by Five-membered Heterocycle Spacer

Han

Wang

2021

Preprint

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“…较高. 将有机溶剂甲苯与绿色溶剂 ScCO 2 中得到的炔-腈环加成反应结果进行了对比(表 3, Entries 5～7) [16] , 可以看出, 反应的化学选择性主要取决于催化剂的种类和活性, 而溶剂仅对反应主产物的产率影响较大.…”

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Carbonyl Cobalt-Catalyzed Cyclotrimerization of Terminal Alkynes in Supercritical Carbon Dioxide

Wang¹,

Yin²,

Guo³

et al. 2019

Chinese Journal of Organic Chemistry

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Atom-efficient [2＋2＋2] cycloaddition reaction of alkynes in green solvent supercritical carbon dioxide (ScCO 2) is an environmentally friendly reaction process that conforms to the principles of green chemistry. Cyclotrimerization of terminal alkynes catalyzed by Co 2 (CO) 8 in pure ScCO 2 has been studied to obtain 1,2,4-trisubstituted benzene derivatives with excellent selectivity. The reaction conditions for the cyclotrimerization were optimized, such as concentration of catalyst, CO 2 pressure, reaction temperature and time. The solubility and phase behavior of the reaction materials and catalysts in ScCO 2 medium were discussed, and the mechanism of Co 2 (CO) 8 catalyzed cyclotrimerization of terminal alkynes was assumed. The reaction substrate was extended from C≡C (alkyne) to C≡N (nitrile), and the alkyne-nitrile cycloaddition reaction in ScCO 2 was preliminary explored. Our optimized catalytic system for the cyclotrimerization of terminal alkynes exhibited wide substrate scope and high product selectivity, in which no organic co-solvent or additives were added. It provided a green synthetic method for 1,2,4-trisubstituted benzenes.

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Cobalt‐Catalyzed [2 + 2 + 2] Cycloaddition Reactions

Glasel,

Hapke

2023

Patai's Chemistry of Functional Groups

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Cobalt‐catalyzed [2 + 2 + 2] cycloaddition reactions are an important tool for the assembly of carbo‐ and hetero‐cyclic ring systems from simple precursor molecules such as alkynes, alkenes, nitriles, and other heterocumulenes such as isocyanates. Cyclopentadienyl (Cp)‐cobalt complexes are still one of the most important classes of catalysts, but in situ generated cobalt catalyst systems are becoming increasingly important for the assembly of achiral as well as chiral target molecules from a large variety of substrates. Substrates comprise simple terminal as well as internal alkynes, diynes, and higher oligoynes and also allow target‐oriented syntheses of unusually large as well as highly substituted molecules as well as natural product synthesis with a cyclotrimerization as the key step of the synthetic sequence. The utilization of olefins as cyclization partners allows the synthesis of products with lesser degree of unsaturation such as cyclohexadienes, cyclohexenes, and dihydropyridines, just to name a view examples. Chiral catalyst systems allow the enantioselective synthesis of biaryls and products with central chirality, and chiral starting materials allow the synthesis of diastereomeric helicenes in an efficient manner. Novel catalysts and reaction engineering allow reaction conditions such as conventional thermal or microwave heating, photochemically assisted cyclizations, and the use of plug‐flow reactors.

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Synthesis, structure and electrochemistry of new diferrocenyl pyridine derivatives

Cited by 9 publications

References 32 publications

The Intramolecular Electronic Interaction Regulated by Five-membered Heterocycle Spacer

The Intramolecular Electronic Interaction Regulated by Five-membered Heterocycle Spacer

Carbonyl Cobalt-Catalyzed Cyclotrimerization of Terminal Alkynes in Supercritical Carbon Dioxide

Cobalt‐Catalyzed [2 + 2 + 2] Cycloaddition Reactions

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