Dibenzopleiadiene-embeded polyaromatics via [4 + 3] annulative decarbonylation/decarboxylation

Kantarod, Kritchasorn; Worakul, Thanapat; Soorukram, Darunee; Kuhakarn, Chutima; Reutrakul, Vichai; Surawatanawong, Panida; Wattanathana, Worawat; Leowanawat, Pawaret

doi:10.1039/d0qo00942c

Cited by 24 publications

(96 citation statements)

References 70 publications

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“…Appealingly, this reaction was found to tolerate a variety of aryl substituents, including those which can be subsequently employed for further π‐extension. A decarboxylative variant of this reaction was also disclosed by Leowanawat in 2020, who obtained similar products using 1,8‐naphthalic anhydride derivatives as starting materials in place of diboronic acids [91b] …”

Section: Metal‐promoted Reactionsmentioning

confidence: 75%

Construction of Heptagon‐Containing Molecular Nanocarbons

et al. 2021

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Molecular nanocarbons containing heptagonal rings have attracted increasing interest due to their dynamic behavior, electronic properties, aromaticity, and solid‐state packing. Heptagon incorporation can not only induce negative curvature within nanocarbon scaffolds, but also confer significantly altered properties through interaction with adjacent non‐hexagonal rings. Despite the disclosure of several beautiful examples in recent years, synthetic strategies toward heptagon‐embedded molecular nanocarbons remain relatively limited due to the intrinsic challenges of heptagon formation and incorporation into polyarene frameworks. In this Review, recent advances in solution‐mediated and surface‐assisted synthesis of heptagon‐containing molecular nanocarbons, as well as the intriguing properties of these frameworks, will be discussed.

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Section: Metal‐promoted Reactionsmentioning

confidence: 75%

Construction of Heptagon‐Containing Molecular Nanocarbons

et al. 2021

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“…Anhydrous DMSO was supplied by Sigma-Aldrich and used without additional purification. 1 H NMR spectra were recorded at 400 MHz, 13 C NMR spectra were recorded at 100 MHz, and 19 F NMR spectra were recorded at 376 MHz. Chemical shifts are reported in parts per million (ppm).…”

Section: Methodsmentioning

confidence: 99%

“…Chemical shifts are reported in parts per million (ppm). 1 H and 13 C chemical shifts are referenced relative to residual solvent signal. High resolution mass spectra were recorded on maXis spectrometer and MicroTOF-Q both from Bruker Daltronics with electrospray ionization (ESI) in positive mode and Agilent 7200 Accurate Mass Q-TOF GC/MS with electron impact ionization (EI).…”

Section: Methodsmentioning

confidence: 99%

“…mp = 248-249 o C. 1 H NMR (400 MHz, DMSO-d6) δ 9.28 (s, 1H), 8.67 (d, J = 1.6 Hz, 1H), 8.43 (d, J = 8.4 Hz, 1H), 8.35 (dd, J = 8.4, 2 Hz, 1H), 7.45 (s, 1H), 3.92 (s, 3H). 13 C NMR (100 MHz, DMSO-d6) δ 164. 4, 138.3, 136.4, 132.9, 132.3, 131.9, 129.1, 117.2, 113.1, 98.9, 52.9.…”

Section: Bmentioning

confidence: 99%

“…6f,6g,12 Indeed, the only several examples of five-membered electron-rich heterocycles connected with low availability of starting materials and complexity of iodine oxidation. 12,13 Only recently, Nachtsheim developed a facile approach to the preparation of iodine-containing heterocycles bearing pyrazole moieties 5 (Fig. 1, b).…”

Section: Introductionmentioning

confidence: 99%

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Preparation and Synthetic Applicability of Novel Imidazole-Containing Cyclic Iodonium Salts

Nikita¹,

Vlasenko²,

Yoshimura³

et al. 2021

Preprint

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The novel approach to the preparation of imidazole-substituted cyclic iodonium salts has been developed via oxidative cyclization of 1-phenyl-5-iodoimidazole using cheap and available Oxone®/H2SO4 oxidative system. The structure of newly prepared compounds has been proved by X-ray monocrystal diffractometry revealing the characteristic surface features for cyclic iodonium salts. The prepared compounds demonstrated the high reactivity in the heterocyclization reactions with elemental sulfur affording benzo[5,1-b]imidazothiazoles with good yields.

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Cyclic Diaryliodonium Salts: Eco‐Friendly and Versatile Building Blocks for Organic Synthesis

Cheng

Guo

2023

Adv Synth Catal

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Cyclic diaryliodoniums are an important class of high‐valent aromatic iodine reagents for the synthesis of various axially chiral biaryls and biaryl compounds. Moreover, transition‐metal‐catalyzed annulation has been established for the construction of various heterocyclic rings and ladder‐type π‐conjugated polycyclic aromatic hydrocarbons with readily available cyclic diaryliodoniums as the starting materials. As halogen‐bonding donors, cyclic aryliodoniums have been explored as organocatalysts in a variety of organic reactions. In this review, the application progress of cyclic diaryliodoniums has been systematically outlined, which highlights recent developments in the application reactions of cyclic diaryliodoniums, including synthetic application, limitations and reaction mechanisms in representative cascade reactions to provide insights for the development prospects of cyclic diaryliodoniums.

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Dibenzopleiadiene-embeded polyaromatics via [4 + 3] annulative decarbonylation/decarboxylation

Abstract: A novel and efficient sequential cross-coupling/annulation strategy is developed to construct structurally and optoelectronically diverse class of dibezopleiadiene-embeded polyaromatics.

Cited by 24 publications

References 70 publications

Construction of Heptagon‐Containing Molecular Nanocarbons

Construction of Heptagon‐Containing Molecular Nanocarbons

Preparation and Synthetic Applicability of Novel Imidazole-Containing Cyclic Iodonium Salts

Cyclic Diaryliodonium Salts: Eco‐Friendly and Versatile Building Blocks for Organic Synthesis

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