Carbazole based Electron Donor Acceptor (EDA) catalysis for the synthesis of biaryl and aryl–heteroaryl compounds

Saritha, R. K.; Annes, Sesuraj Babiola; Saravanan, S.; Ramesh, Subburethinam

doi:10.1039/d0ob00282h

Cited by 13 publications

(14 citation statements)

References 34 publications

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“…The compound was purified by column chromatography (silica gel 100–200 mesh) with 1% ethyl acetate in hexane to give the product as a colorless solid (yield: 110 mg, 63%). Spectroscopic data matched with the literature …”

Section: Methodsmentioning

confidence: 72%

Pyrazole-Mediated C–H Functionalization of Arene and Heteroarenes for Aryl–(Hetero)aryl Cross-Coupling Reactions

et al. 2021

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Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C–C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

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Section: Methodsmentioning

confidence: 72%

Pyrazole-Mediated C–H Functionalization of Arene and Heteroarenes for Aryl–(Hetero)aryl Cross-Coupling Reactions

et al. 2021

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“…The mechanism for this reaction was not further investigated, although it could be possible that the EDA complex between 1 and 4 or 2 could be activated thermally to some degree, as has been reported for other systems. 57 , 58 …”

Section: Resultsmentioning

confidence: 99%

Aerobic Oxidative EDA Catalysis: Synthesis of Tetrahydroquinolines Using an Organocatalytic EDA Active Acceptor

Runemark

Sundén

2022

J. Org. Chem.

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A catalytic electron donor–acceptor (EDA) complex for the visible-light-driven annulation reaction between activated alkenes and N,N-substituted dialkyl anilines is reported. The key photoactive complex is formed in situ between dialkylated anilines as donors and 1,2-dibenzoylethylene as a catalytic acceptor. The catalytic acceptor is regenerated by aerobic oxidation. Investigations into the mechanism are provided, revealing a rare example of a catalytic acceptor in photoactive EDA complexes that can give access to selective functionalization of aromatic amines under mild photochemical conditions.

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“…Similarly, the HOMO of CSR 2 is located in the carbazole moiety, whereas the HOMO and LUMO of BSR 2 and DSR 2 are located in the naphthalene and imidazoline-2-thione moieties. The difference originates from the introduction of the carbazole moiety, which is known as a strong donor and fluorescence quencher ( Ledwon, 2019 ; Rehmat et al, 2020 ; Saritha et al, 2020 ). Thus, the energy gap between the LUMO and the HOMO (E g ) of CIR 2 (1.80–2.03 eV) is significantly lower than those of BIR 2 and DIR 2 (3.77–3.86 eV).…”

Section: Resultsmentioning

confidence: 99%

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications

et al. 2021

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The ability to detect hypochlorite (HOCl/ClO−) in vivo is of great importance to identify and visualize infection. Here, we report the use of imidazoline-2-thione (R1SR2) probes, which act to both sense ClO− and kill bacteria. The N2C=S moieties can recognize ClO− among various typical reactive oxygen species (ROS) and turn into imidazolium moieties (R1IR2) via desulfurization. This was observed through UV–vis absorption and fluorescence emission spectroscopy, with a high fluorescence emission quantum yield (ՓF = 43–99%) and large Stokes shift (∆v∼115 nm). Furthermore, the DIM probe, which was prepared by treating the DSM probe with ClO−, also displayed antibacterial efficacy toward not only Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) but also methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum ß-lactamase–producing Escherichia coli (ESBL-EC), that is, antibiotic-resistant bacteria. These results suggest that the DSM probe has great potential to carry out the dual roles of a fluorogenic probe and killer of bacteria.

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Carbazole based Electron Donor Acceptor (EDA) catalysis for the synthesis of biaryl and aryl–heteroaryl compounds

Abstract: A highly regioselective, carbazole based electron donor acceptor (EDA) catalyzed synthesis of biaryl and aryl–heteroaryl compounds is described.

Cited by 13 publications

References 34 publications

Pyrazole-Mediated C–H Functionalization of Arene and Heteroarenes for Aryl–(Hetero)aryl Cross-Coupling Reactions

Pyrazole-Mediated C–H Functionalization of Arene and Heteroarenes for Aryl–(Hetero)aryl Cross-Coupling Reactions

Aerobic Oxidative EDA Catalysis: Synthesis of Tetrahydroquinolines Using an Organocatalytic EDA Active Acceptor

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications

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