Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Ortho C-H arylation of arenes at room temperature using visible light ruthenium C-H activation.

ABSTRACT: A ruthenium-catalyzed ortho C-H arylation process is described using visible light. Using the readily available catalyst [RuCl₂(p-cymene)]₂, visible light irradiation was found to enable arylation of 2-aryl-pyridines at room temperature for a range of aryl bromides and iodides.

SUBMITTER: Sagadevan A

PROVIDER: S-EPMC8159458 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Ortho C-H arylation of arenes at room temperature using visible light ruthenium C-H activation.

Sagadevan Arunachalam A Charitou Anastasios A Wang Fen F Ivanova Maria M Vuagnat Martin M Greaney Michael F MF

Chemical science 20200407 17

A ruthenium-catalyzed ortho C-H arylation process is described using visible light. Using the readily available catalyst [RuCl2(p-cymene)]2, visible light irradiation was found to enable arylation of 2-aryl-pyridines at room temperature for a range of aryl bromides and iodides. ...[more]

PMID: 34122900

Similar Datasets

Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes.

Project description:The first visible light-induced Pd-catalyzed Heck reaction of α-heteroatom substituted alkyl iodides and -bromides with vinyl arenes/heteroarenes has been developed. This transformation efficiently proceeds at room temperature and enables synthesis of valuable functionalized allylic systems, such as allylic silanes, boronates, germanes, stannanes, pivalates, phosphonates, phthalimides, and tosylates from the corresponding α-substituted methyl iodides. Notably, synthesis of the latter substrates failed under existing thermally induced Pd-catalyzed conditions, which highlights the importance of visible light for this transformation.

| S-EPMC5728111 | biostudies-literature

Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis.

Project description:This communication describes the development of a room-temperature ligand-directed C-H arylation reaction using aryldiazonium salts. This was achieved by the successful merger of palladium-catalyzed C-H functionalization and visible-light photoredox catalysis. The new method is general for a variety of directing groups and tolerates many common functional groups.

| S-EPMC3222896 | biostudies-literature

Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis.

Project description:Employing sulfonyl azide as a nitrogen donor, a visible-light-enabled aerobic dealkylative imidation of tertiary and secondary amines involving C(sp3)-C(sp3) bond cleavage with moderate to excellent yields at room temperature is described. It has been demonstrated that this imidation could take place spontaneously upon visible-light irradiation, and could be facilitated considerably by a ruthenium photocatalyst and oxygen. An alternative mechanism to the previous aerobic photoredox pathway has also been proposed.

| S-EPMC9033495 | biostudies-literature

Tuning ferromagnetism at room temperature by visible light.

Project description:Most digital information today is encoded in the magnetization of ferromagnetic domains. The demand for ever-increasing storage space fuels continuous research for energy-efficient manipulation of magnetism at smaller and smaller length scales. Writing a bit is usually achieved by rotating the magnetization of domains of the magnetic medium, which relies on effective magnetic fields. An alternative approach is to change the magnetic state directly by acting on the interaction between magnetic moments. Correlated oxides are ideal materials for this because the effects of a small external control parameter are amplified by the electronic correlations. Here, we present a radical method for reversible, light-induced tuning of ferromagnetism at room temperature using a halide perovskite/oxide perovskite heterostructure. We demonstrate that photoinduced charge carriers from the [Formula: see text] photovoltaic perovskite efficiently dope the thin [Formula: see text] film and decrease the magnetization of the ferromagnetic state, allowing rapid rewriting of the magnetic bit. This manipulation could be accomplished at room temperature; hence this opens avenues for magnetooptical memory devices.

| S-EPMC7104399 | biostudies-literature

Visible-Light-Excited Room Temperature Phosphorescent Carbon Dots.

Project description:Carbon dots (CDs) with a room temperature phosphorescent (RTP) feature have attracted considerable interest in recent years due to their fundamental importance and promising applications. However, the reported matrix-free RTP CDs only show short-wavelength (green to yellow) emissions and have to be triggered by ultraviolet (UV) light (below 400 nm), limiting their applications in certain fields. Herein, visible-light-excited matrix-free RTP CDs (named AA-CDs) with a long-wavelength (orange) emission are reported for the first time. The AA-CDs can be facilely prepared via a microwave heating treatment of L-aspartic acid (AA) in the presence of ammonia and they emit unique orange RTP in the solid state with visible light (420 nm) excitation just being switched off. Through the studies of the carbonization process, the C=O and C=N containing moieties in the AA-CDs are confirmed to be responsible for the observed RTP emission. Finally, the applications of AA-CDs in information encryption and anti-counterfeiting were preliminarily demonstrated.

| S-EPMC7153588 | biostudies-literature

N-Acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes.

Project description:This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.

| S-EPMC4004272 | biostudies-literature

Site-Selective C-H Arylation of Diverse Arenes Ortho to Small Alkyl Groups.

Project description:Catalytic systems for direct C-H activation of arenes commonly show preference for electronically activated and sterically exposed C-H sites. Here we show that a range of functionally rich and pharmaceutically relevant arene classes can undergo site-selective C-H arylation ortho to small alkyl substituents, preferably endocyclic methylene groups. The C-H activation is experimentally supported as being the selectivity-determining step, while computational studies of the transition state models indicate the relevance of non-covalent interactions between the catalyst and the methylene group of the substrate. Our results suggest that preference for C(sp2 )-H activation next to alkyl groups could be a general selectivity mode, distinct from common steric and electronic factors.

| S-EPMC9805285 | biostudies-literature

Visible-Light-Mediated Photoredox-Catalyzed N-Arylation of NH-Sulfoximines with Electron-Rich Arenes.

Project description:The direct C-H/N-H dehydrogenative cross-coupling of NH-sulfoximines with electron-rich arenes was realized by oxidative visible-light photoredox catalysis, applying 9-mesityl-10-methylacridinium perchlorate as an organic photocatalyst. Sulfoximines display diverse desirable properties for medicinal chemistry and the pharmaceutical industry. However, their preparation is still challenging. Our reaction proceeds without sacrificial oxidant, at room temperature and is highly selective for the C-N bond forming reaction. The scope of the reaction includes mono- and multi-alkylated and halogenated arenes, which are reacted with aromatic and aliphatic electron-rich and electron-poor NH-sulfoximines, giving moderate to excellent yields of the N-arylated sulfoximines. In addition, we successfully conducted the developed reaction on a gram scale (1.5 g). Mechanistic investigations show that both arene and NH-sulfoximine interact with the excited-state of the photocatalyst. We propose a radical-based mechanism, where both the arene and the NH-sulfoximine are photo-oxidized to their respective radical intermediates. Radical-radical cross-coupling subsequently leads to the N-arylated sulfoximine. Two electrons and two protons are released during the reaction and are subsequently converted into H2 by a proton-reducing cobalt-catalyst.

| S-EPMC6175368 | biostudies-literature

Tuning reactivity and site selectivity of simple arenes in C-H activation: ortho-arylation of anisoles via arene-metal π-complexation.

Project description:Current approaches to achieve site selectivity in the C-H activation of arenes involve the use of directing groups or highly electron-poor arenes. In contrast, simple arenes, such as anisole, are characterized by poor reactivity and selectivity. We report that π-complexation to a Cr(CO)3 unit enhances the reactivity of anisoles providing an unprecedented ortho-selective arylation. This mild methodology can be used for the late stage functionalization of bioactive compounds containing the anisole motif, allowing the construction of novel organic scaffolds with few synthetic steps.

| S-EPMC4379957 | biostudies-literature

Room temperature, metal-free arylation of aliphatic alcohols.

Project description:Diaryliodonium salts are demonstrated as efficient arylating agents of aliphatic alcohols under metal-free conditions. The reaction proceeds at room temperature within 90 min to give alkyl aryl ethers in good to excellent yields. Aryl groups with electron-withdrawing substituents are transferred most efficiently, and unsymmetric iodonium salts give chemoselective arylations. The methodology has been applied to the formal synthesis of butoxycaine.

| S-EPMC4000167 | biostudies-literature