Recent Progress Concerning the N-Arylation of Indoles

Oeser, Petr; Koudelka, Jakub; Petrenko, Artem; Tobrman, Tomáš

doi:10.3390/molecules26165079

Cited by 17 publications

(9 citation statements)

References 194 publications

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“…13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 139.7, 135.8, 129.5, 129.3, 127.9, 126.3, 124.3, 122.3, 121.1, 120.3, 110.4, 103.5. The spectral data were in accordance with the literature …”

Section: Methodssupporting

confidence: 66%

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NBE-Controlled Palladium-Catalyzed Intermolecular Selective C–H Silylation of Boronic Acids

Li,

Yu,

Zhang

et al. 2023

J. Org. Chem.

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An efficient palladium-catalyzed intermolecular selective C–H silylation of boronic acids is described. The combination of palladium catalyst with copper oxidant enables ortho-selective C–H silylation by employing hexamethyldisilane as the trimethylsilyl source, which relies on the control of NBE derivatives as a switch, thus providing straightforward access to divergent organosilicon compounds.

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“…13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 139.7, 135.8, 129.5, 129.3, 127.9, 126.3, 124.3, 122.3, 121.1, 120.3, 110.4, 103.5. The spectral data were in accordance with the literature …”

Section: Methodssupporting

confidence: 66%

“…The spectral data were in accordance with the literature. 24 Benzo [b]thiophene (7). Title compound was prepared according to the literature 7c (petroleum ether) as a white solid, isolated yield 55% (15 mg).…”

Section: Trimethyl(2-((2r3r)-3-(trimethylsilyl)bicyclo[221]heptan-2-y...mentioning

confidence: 99%

NBE-Controlled Palladium-Catalyzed Intermolecular Selective C–H Silylation of Boronic Acids

Li,

Yu,

Zhang

et al. 2023

J. Org. Chem.

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“…However, the possibilities of C-N -based multiple cross-couplings of polychlorinated benzenes were never studied in detail according to our best knowledge. Merely differences in cross-couplings of aromates substituted with different halides (typically bromoiodobenzenes, bromo-chlorobenzenes and halogeno-fluorobenzenes) were mentioned in published articles [59,60,70,[128][129][130][131][132][133][134][135].…”

Section: Discussionmentioning

confidence: 99%

Copper-Catalyzed Reactions of Aryl Halides with N-Nucleophiles and Their Possible Application for Degradation of Halogenated Aromatic Contaminants

2022

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This review summarizes recent applications of copper or copper-based compounds as a nonprecious metal catalyst in N-nucleophiles-based dehalogenation (DH) reactions of halogenated aromatic compounds (Ar-Xs). Cu-catalyzed DH enables the production of corresponding nonhalogenated aromatic products (Ar-Nu), which are much more biodegradable and can be mineralized during aerobic wastewater treatment or which are principally further applicable. Based on available knowledge, the developed Cu-based DH methods enable the utilization of amines for effective cleavage of aryl-halogen bonds in organic solvents or even in an aqueous solution.

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“…2a However, indole, a common pyrrole-based mono-nitrogen heterocycle, exhibits poor reactivity towards N-arylation with boronic-acid under ambient conditions. [14] To address the issue of poor N-arylation of indole in ambient conditions, we chose 7azaindole, a di-nitrogen heterocycle and an isostere of indole with significant biological importance and an intriguing chelating capability to the metal ions through fused pyridine and pyrrole ring nitrogens. [15] The advantage of 7-azaindole over indole is that it can provide a weaker second donation through π-acidic pyridine ring along with the pyrrolo nitrogen to the metal center.…”

Section: Introductionmentioning

confidence: 99%

Exploiting Coordination Behavior of 7‐Azaindole for Mechanistic Investigation of Chan‐Lam Coupling and Application to 7‐Azaindole Based Pharmacophores

Mondal

Mukhopadhyay

Sengupta

et al. 2023

Chemistry A European J

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Multiple spectroscopic techniques, along with single-crystal X-ray analysis, have been used to reveal the detailed structural and electronic information on reaction intermediates of a new copper(II)-DBU catalytic system for the N-arylation of 7-Azaindole. The reaction mixture of Chan-Lam cross-coupling yields two dimeric copper(II)-7-azaindole complexes, including one attached with DBU, prior to adding arylboronic acid and are confirmed structurally and spectroscopically. A suitable mechanism has been proposed using the dimeric copper(II) complex as a catalyst for the coupling reactions. The role of DBU as a base and also as an auxiliary ligand in the course of the reaction has been established. The transmetalated monomeric aryl-copper(II) species generated from the dimeric unit is oxidized by another equivalent of copper(II) to yield an aryl-copper(III) intermediate for facile Narylation, which has been authenticated with UV-vis spectroscopy. The regeneration of the copper(II)-catalyst by aerial oxidation of colorless copper(I) species (generated via reductive elimination and disproportionation step) is confirmed by mass and absorption spectroscopy. Detailed DFT and TD-DFT calculations help to rationalize the proposed reaction intermediates and their corresponding electronic transitions. Moreover, the confirmation of copper(I)-7-azaindole intermediate via HRMS reaffirmed the involvement of Cu(II)/Cu(III)/ Cu(I) species in the Chan-Lam type of coupling. A medicinallyimportant 7-azaindole-based SHP2 inhibitor has been synthesized via sequential arylation.

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Recent Progress Concerning the N-Arylation of Indoles

Cited by 17 publications

References 194 publications

NBE-Controlled Palladium-Catalyzed Intermolecular Selective C–H Silylation of Boronic Acids

NBE-Controlled Palladium-Catalyzed Intermolecular Selective C–H Silylation of Boronic Acids

Copper-Catalyzed Reactions of Aryl Halides with N-Nucleophiles and Their Possible Application for Degradation of Halogenated Aromatic Contaminants

Exploiting Coordination Behavior of 7‐Azaindole for Mechanistic Investigation of Chan‐Lam Coupling and Application to 7‐Azaindole Based Pharmacophores

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