CH Activation of Indoles DOI
Rafał Kowalczyk,

Lalit S. Mittal

Handbook of CH‐Functionalization, Journal Year: 2022, Volume and Issue: unknown, P. 1 - 147

Published: Oct. 2, 2022

Abstract Tremendous advances in transition metal‐catalyzed CH functionalization of the indole scaffolds have been recently reported. Great efforts devoted to directing group strategy development selectivity achievement overriding both inherent reactivity scaffold and activation C2/C3H bonds. This article aims highlight elegant methods enabling direct arylation, alkenylation, alkylation, alkynylation along with introduction heteroatoms into via selective strategies.

Language: Английский

Transition metal-catalyzed C–H functionalizations of indoles DOI
Pravin Kumar, Prajyot Jayadev Nagtilak, Manmohan Kapur

et al.

New Journal of Chemistry, Journal Year: 2021, Volume and Issue: 45(31), P. 13692 - 13746

Published: Jan. 1, 2021

This review summarises a wide range of transformations on the indole skeleton, including arylation, alkenylation, alkynylation, acylation, nitration, borylation, and amidation, using transition-metal catalyzed C–H functionalization as key step.

Language: Английский

Citations

73
Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations DOI Creative Commons

Seungmin Lee,

Minsuk Kim,

Hyewon Han

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 200 - 216

Published: Jan. 22, 2025

Over the past decade, dioxazolones have been widely used as N -acylamide sources in amidation processes of challenging substrates, typically employing precious transition metals. However, these catalytic systems often present several challenges associated with cost, toxicity, stability, and recyclability. Among 3d metals, copper catalysts gaining increasing attention owing to their abundance, cost-effectiveness, sustainability. Recently, applied chemical transformation dioxazolones, conferring a convenient protocol towards amidated products. This review highlights recent advancements synthetic transformations particular examples salts.

Language: Английский

Citations

0
Rhodium(III)‐Catalyzed Direct C7‐Selective Alkenylation and Alkylation of Indoles with Maleimides DOI

Yaoguang Sheng,

Yi Gao, Bingbing Duan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 364(2), P. 307 - 313

Published: Nov. 6, 2021

Abstract A versatile and efficient method for the coupling of maleimides indoles at C7‐position has been established under Rh(III) catalysis. The present protocol was compatible with various functional groups, diverse 3‐(indol‐7‐yl)maleimides 3‐(indol‐7‐yl)succinimides were obtained in moderate to excellent yields by switching reaction conditions. Moreover, this further highlights unique practical application conjugation pharmaceutically useful compounds amino acid derivatives. To explore mechanism transformation, deuteration studies control experiments have carried out. magnified image

Language: Английский

Citations

19
Small-Molecule Compound SYG-180-2-2 to Effectively Prevent the Biofilm Formation of Methicillin-Resistant Staphylococcus aureus DOI Creative Commons

Lulin Rao,

Yaoguang Sheng,

Jiao Zhang

et al.

Frontiers in Microbiology, Journal Year: 2022, Volume and Issue: 12

Published: Jan. 7, 2022

The resistance of methicillin-resistant Staphylococcus aureus (MRSA) has augmented due to the abuse antibiotics, bringing about difficulties in treatment infection especially with formation biofilm. Thus, it is essential develop antimicrobials. Here we synthesized a novel small-molecule compound, which termed SYG-180-2-2 (C21H16N2OSe), that had antibiofilm activity. aim this study was demonstrate effect against clinical MRSA isolates at subinhibitory concentration (4 μg/ml). In study, showed significant suppression biofilm occurred treatment, inhibition ranged between 65.0 and 85.2%. Subsequently, confocal laser scanning microscopy bacterial metabolism activity assay further demonstrated could suppress Additionally, reduced adhesion polysaccharide intercellular adhesin (PIA) production. It found expression icaA other biofilm-related genes were downregulated as evaluated by RT-qPCR. At same time, icaR codY upregulated when biofilms treated SYG-180-2-2. Based on above results, speculate inhibits affecting cell related PIA Above all, no toxic effects human normal alveolar epithelial cells BEAS-2B. Collectively, compound safe effective antibacterial agent for inhibiting

Language: Английский

Citations

14
Multideuteration of Nitroaromatics by Silver-Catalyzed Hydrogen-Isotope Exchange DOI
Jianbo Tang,

Junhua Kong,

Hui Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(3), P. 1560 - 1567

Published: Jan. 12, 2023

Silver-catalyzed deuteration of nitroaromatics has been achieved using D2O as the deuterium source. Distinct from well-established directing group-guided hydrogen-isotope exchange, this protocol showed an interesting pattern, where considerable accumulation was observed around aromatic rings. Controlling experiments suggested that initiated by a silver-promoted C–H activation. Therefore, tentative two-stage mechanism involving aryl-silver species proposed to explain on meta- and para-positions.

Language: Английский

Citations

7
Recent advances in ruthenium‐catalysed aromatic C−H bond oxygenation, nitrogenation and halogenation DOI
Keisham S. Singh

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(7)

Published: Feb. 13, 2024

Abstract The transition metal‐catalysed C−H bond functionalization has emerged as a powerful tool for accessing numerous organic compounds in greener manner with step and atom economy. Remarkable progress been made the during past decades trend is continuing new reactions are being added. In functionalization, growing attention paid on ruthenium, particularly, stable ruthenium(II) it allows several to perform water high selectivity. ruthenium‐catalysed reactions, such arylation, alkenylation, annulation, cyanation, amination silylation just mention some have well documented published papers, book chapters review articles. However, rapidly, comprehensive necessary from time highlight this ever expanding field. view of this, manuscript presents direct C−O, C−N C‐halogen forming involving aromatic covering oxygenation, amination, amidation, imidation, nitration halogenation reported 2012 2022.

Language: Английский

Citations

2
Iron‐catalyzed C‐7 Selective NH2 Amination of Indoles DOI

Zhanlin Wang,

Jin-Kai Cheng,

Fei Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)

Published: July 9, 2024

7-Aminoindoles are important synthetic intermediates to a broad range of bioactive molecules. Transition metal-catalyzed directed C-H amination is among the most straightforward route for their synthesis, whereas methods that could directly incorporate an NH

Language: Английский

Citations

2
Pd(II)-Catalyzed C4-Selective Alkynylation of Indoles by a Transient Directing Group DOI

Ze-Xuan Zhang,

Bing Zhang, Meng Yuan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6819 - 6824

Published: Aug. 6, 2024

With alanine as a transient directing group, Pd-catalyzed regioselective alkynylation at the indole C4-position was successfully established in good yield. The total synthesis of PAF antagonist demonstrated synthetic utility this protocol. regioselectivity explicitly proven by prepared C4-selective palladacycle intermediate catalytic process and DFT calculation energy barriers C4- C2-site-selective C-H activation indole.

Language: Английский

Citations

2
Regioselective peri-C–H selenylation of aromatic compounds with weakly coordinating ketone groups DOI
Bingbing Duan, Yao Wu, Yi Gao

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(82), P. 11555 - 11558

Published: Jan. 1, 2022

A novel and versatile method for peri-C-H selenylation of aromatic compounds bearing ketone groups, including chromones, xanthones, acridinones, quinolinones naphthoquinones with diselenides under Ru(II) catalysis is presented. Various chromones are applicable this transformation, affording 5-selenyl in a highly regioselective manner good to excellent yields. This transformation easy scale up the desired products can be further modified. Most importantly, allows late-stage bioactive compounds. Mechanistic studies show that radicals may involved transformation.

Language: Английский

Citations

11
Sulfur-Directed C7-Selective Alkenylation of Indoles under Rhodium Catalysis DOI

Chandrababu Naidu Kona,

Yuji Nishii, Masahiro Miura

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(16), P. 6252 - 6256

Published: Aug. 5, 2021

Regioselective direct functionalization of an indole benzenoid fragment has been a significant challenge because its inherently lower reactivity. In this report, we introduce Rh-catalyzed C7-selective alkenylation derivatives using new sulfur directing group N-SCy. A notable feature system is that the readily installed to indoles and easily removed after catalysis under mild conditions.

Language: Английский

Citations

14