The Diels–Alder reaction in the synthesis of fused heterocyclic aromatic compounds

Dyan, Ok Ton; Zaikin, Pavel A.

doi:10.1007/s10593-023-03183-1

Cited by 3 publications

(1 citation statement)

References 33 publications

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“…Traditional approaches to thiophene 1,1-dioxides include oxidation of thiophenes by peroxides, , Diels–Alder reactions, and C–X/C–M cross-couplings (Stille coupling, Suzuki–Miyaura coupling, etc.) .…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed C2-Selective Direct Arylation of Benzo[b]thiophene 1,1-Dioxides with Arylboronic Acids

Zhang,

Lu,

Wang

et al. 2023

ACS Omega

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A novel oxidative cross-coupling of benzo[b]thiophene 1,1-dioxides with arylboronic acids was reported. The efficient reaction occurred at the C2-position via C–H activation, followed by Pd(II)-catalyzed arylation. Furthermore, a series of C2-arylated products with significant photoluminescence properties have been synthesized and characterized, which illustrates the potential applications of our method in the aggregation-induced emission field.

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Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed C2-Selective Direct Arylation of Benzo[b]thiophene 1,1-Dioxides with Arylboronic Acids

Zhang,

Lu,

Wang

et al. 2023

ACS Omega

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Construction of the Red‐Green‐Blue Luminescence Conversion System Based on Donor‐Acceptor Dyes Exchange with Diels‐Alder Dynamic Covalent Bonds

Zheng,

Zhang,

Zhang

et al. 2024

ChemPhotoChem

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The construction of full‐color fluorescence systems has received widespread attention because of their applications in lighting materials, optoelectronic materials, and fluorescent probes. However, for the full‐color luminescence system based on trichromatic materials, there are no connections between materials of different luminescent colors. Herein, A new donor‐acceptor dye with red fluorescence was synthesized. The dye displays excellent optical properties of short half‐peak width and strong fluorescence emission. An effective energy transfer process from the dansyl donor to the acceptor was observed with a transfer efficiency of 81%. Further, dyes with green and blue fluorescence were introduced to construct a full‐spectrum fluorescent system. Through exchange reactions of Diels‐Alder dynamic covalent bonds, red, green, and blue luminescence can be converted. This work provides a new idea for the design of full‐color fluorescent materials.

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A New Insight into the Molecular Mechanism of the Reaction between 2-Methoxyfuran and Ethyl (Z)-3-phenyl-2-nitroprop-2-enoate: An Molecular Electron Density Theory (MEDT) Computational Study

Sadowski,

Dresler,

Wróblewska

et al. 2024

Molecules

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The molecular mechanism of the reaction between 2-methoxyfuran and ethyl (Z)-3-phenyl-2-nitroprop-2-enoate was investigated using wb97xd/6-311+G(d,p)(PCM) quantum chemical calculations. It was found that the most probable reaction mechanism is fundamentally different from what was previously postulated. In particular, six possible zwitterionic intermediates were detected on the reaction pathway. Their formation is determined by the nature of local nucleophile/electrophile interactions. Additionally, the channel involving the formation of the exo-nitro Diels–Alder cycloadduct was completely ruled out. Finally, the electronic nature of the five- and six-membered nitronates as potential TACs was evaluated.

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The Diels–Alder reaction in the synthesis of fused heterocyclic aromatic compounds

Cited by 3 publications

References 33 publications

Palladium-Catalyzed C2-Selective Direct Arylation of Benzo[b]thiophene 1,1-Dioxides with Arylboronic Acids

Palladium-Catalyzed C2-Selective Direct Arylation of Benzo[b]thiophene 1,1-Dioxides with Arylboronic Acids

Construction of the Red‐Green‐Blue Luminescence Conversion System Based on Donor‐Acceptor Dyes Exchange with Diels‐Alder Dynamic Covalent Bonds

A New Insight into the Molecular Mechanism of the Reaction between 2-Methoxyfuran and Ethyl (Z)-3-phenyl-2-nitroprop-2-enoate: An Molecular Electron Density Theory (MEDT) Computational Study

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