Domino N-/C- or N-/N-/C-arylation of imidazoles to yield polyaryl imidazolium salts via atom-economical use of diaryliodonium salts

Li, Shiqing; Lv, Hongxu; Yu, Yu; Ye, Xiuqing; Li, Baisong; Yang, Songming; Mo, Yanru; Kong, Xiangfei

doi:10.1039/c9cc05237b

Cited by 26 publications

(9 citation statements)

References 54 publications

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“…The reaction of 4 to give 5 represents only the second known synthesis of a phenanthrene-extended triarylimidazolinium ion. 59 This kind of transformation from a dicationic six-member aromatic ring to a cationic five-member aromatic ring is unprecedented to the best of our knowledge and is highly interesting, especially considering that this process arises from the rupture of a C–C double bond. Because extended imidazolinium ions represent a valuable class of molecules because of their potential applications in optoelectronics and sensing, 59 − 61 an investigation on the reaction was carried out.…”

Section: Results and Discussionmentioning

confidence: 99%

Phenanthrene-Extended Phenazine Dication: An Electrochromic Conformational Switch Presenting Dual Reactivity

et al. 2022

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The synthesis and isolation of one of the few examples of a π-extended diamagnetic phenazine dication have been achieved by oxidizing a phenanthrene-based dihydrophenazine precursor. The resulting dication was isolated and fully characterized, highlighting an aromatic distorted structure, generated by the conformational change upon the oxidation of the dihydrophenazine precursor, which is also correlated with a marked electrochromic change in the UV–vis spectrum. The aromaticity of the dication has also been investigated theoretically, proving that the species is aromatic based on all major criteria (structural, magnetic, and energetic). Moreover, the material presents an intriguing dual reactivity, resulting in ring contraction to a π-extended triarylimidazolinium and reduction to the dihydrophenazine precursor, depending on the nature of the nucleophile involved. This result helps shed light on the yet largely unexplored reactivity and properties of extended dicationic polycyclic aromatic hydrocarbons (PAHs). In particular, the fact that the molecule can undergo a reversible change in conformation upon oxidation and reduction opens potential applications for this class of derivatives as molecular switches and actuators.

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Section: Results and Discussionmentioning

confidence: 99%

Phenanthrene-Extended Phenazine Dication: An Electrochromic Conformational Switch Presenting Dual Reactivity

et al. 2022

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“…Treatment of pyrazole derivatives or triazole with unsymmetrical diaryliodonium triflates led to the diarylated compounds with excellent selectivity exhibiting a noteworthy steric and electronic differentiation. A similar powerful domino process using N-heterocycles was recently published by Kong and Li who focused their interest on developing straightforward methods to prepare polyarylated imidazoles via copper-catalyzed domino di/tri-arylation [137]. The main feature was the formation of imidazolium salts also recycling the residual counter anion of the diaryliodoniums thus providing a high atom-economical process.…”

Section: Atom-economical Tandem N-h/ch Arylation Of Heteroarenesmentioning

confidence: 92%

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

2020

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Owing to the pioneering works performed on the metal-catalyzed sp2 C–H arylation of indole and pyrrole by Sanford and Gaunt, N– and C-arylation involving diaryliodonium salts offers an attractive complementary strategy for the late-stage diversification of heteroarenes. The main feature of this expanding methodology is the selective incorporation of structural diversity into complex molecules which usually have several C–H bonds and/or N–H bonds with high tolerance to functional groups and under mild conditions. This review summarizes the main recent achievements reported in transition-metal-catalyzed N– and/or C–H arylation of heteroarenes using acyclic diaryliodonium salts as coupling partners.

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“…[24][25][26][27][28][29][30] Greaney and coworkers recently demonstrated sequential one-pot diarylations with acyclic Ar 2 IX through a tandem, copper-catalyzed C-and N-arylation of indoles in moderate yields. 18,[31][32][33] Although yield drops indeed can be the drawbacks of one-pot reactions, advantages of such systems include increased time-efficiency and reduced waste formation as workup and purification of the intermediate product are avoided. 34 A transition-metal-free, high-yielding diarylation methodology that proceeds through a one-pot reaction under mild conditions would be a sustainable alternative to existing methods.…”

Section: Introductionmentioning

confidence: 99%

Diarylation of N- and O-nucleophiles through a metal-free cascade reaction

Linde

Bulfield

Kervefors

et al. 2022

Chem

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Domino N-/C- or N-/N-/C-arylation of imidazoles to yield polyaryl imidazolium salts via atom-economical use of diaryliodonium salts

Abstract: A Cu-mediated domino di-/triarylation reaction of imidazoles in a single step by using two aryls as well as an anion of a diaryliodonium salt is developed to quickly achieve polyaryl imidazolium salts.

Cited by 26 publications

References 54 publications

Phenanthrene-Extended Phenazine Dication: An Electrochromic Conformational Switch Presenting Dual Reactivity

Phenanthrene-Extended Phenazine Dication: An Electrochromic Conformational Switch Presenting Dual Reactivity

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

Diarylation of N- and O-nucleophiles through a metal-free cascade reaction

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