Ruthenium-catalyzed electrochemical C–H activation for organic synthesis DOI Creative Commons

Rajaram Maayuri,

Parthasarathy Gandeepan

Electrochemistry, Journal Year: 2024, Volume and Issue: unknown, P. 219 - 244

Published: Nov. 27, 2024

Transition metal-catalyzed C–H activation is a powerful tool in organic synthesis, providing high atom and step economy while reducing waste. Among the 4d 5d transition metals, ruthenium stands out for its affordability effectiveness under mild reaction conditions diverse reactions. Recently, advances metallaelectrocatalysis have allowed ruthenium-catalyzed transformations to use electricity instead of traditional oxidants, enhancing selectivity costs This review highlights recent progress electrochemical functionalization reactions, showcasing key developments innovations.

Language: Английский

Discovery of Organic Optoelectronic Materials Powered by Oxidative Ar–H/Ar–H Coupling DOI
Yudong Yang, Yimin Wu, Zhengyang Bin

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(2), P. 1224 - 1243

Published: Jan. 4, 2024

Efficient and streamlined synthetic methods that facilitate the rapid build-up of structurally diverse π-conjugated systems are paramount importance in quest for organic optoelectronic materials. Among these methods, transition-metal-catalyzed oxidative Ar–H/Ar–H coupling reactions between two (hetero)arenes have emerged as a concise effective approach generating wide array bi(hetero)aryl fused heteroaryl structures. This innovative bypasses challenges associated with substrate pre-activation processes, thereby allowing creation frameworks were previously beyond reach using conventional Ar–X/Ar–M reactions. These inherent advantages ushered new design patterns molecules deviate from traditional methods. ground-breaking enables transcendence limitations repetitive material structures, ultimately leading to discovery novel high-performance In this Perspective, we provide an overview recent advances development materials through utilization We introduce several notable strategies domain, covering both directed non-directed strategies, dual chelation-assisted strategy ortho-C–H arylation/cyclization strategy. Additionally, shed light on role advancement Finally, discuss current existing protocols offer insights into future prospects field.

Language: Английский

Citations

21

Electrochemical Synthesis of Heterocyclic Compounds via Carbon–Heteroatom Bond Formation: Direct and Indirect Electrolysis DOI Creative Commons

Yasuyuki Okumura,

Eisuke F. Sato, Koichi Mitsudo

et al.

Chemistry Letters, Journal Year: 2024, Volume and Issue: 53(8)

Published: July 26, 2024

Abstract Electrochemical organic synthesis has attracted attention as an environmentally friendly method for constructing heterocyclic compounds via carbon–heteroatom bond formation. Herein, we describe the representative examples of electrochemical reactions to produce heterocycles and discuss them according whether they involve direct or indirect electrolysis.

Language: Английский

Citations

5

Tandem Electrochemical Oxidation of Polycyclic Aromatic Amines Towards Carbazoles and Phenazine‐based Aza‐helicenes DOI

Boning Yan,

Ming Lei,

Zefeng Tang

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(25)

Published: March 20, 2024

Abstract Experimental and theoretical study of the regioselectivity mechanism polycyclic aromatic amine (PAA) electrochemical oxidation is important for designing nitrogen doped large π‐conjugated functional molecules. Herein, we used binary‐, ternary‐, quaternary‐fused PAAs as electro‐oxidative reaction substrates to investigate yield changes carbazole phenazine based aza‐helicene other than oligomers, which were obtained through pyrrole pyrazine annulation pathways. Combined with restrained electrostatic potential (RESP) steric hindrance factor analysis substrate, electron spin density distribution free radical resonance hybrid population atoms in structure each tautomer indicate that degree delocalized dispersion N resulting change C tautomers determine regioselectivity. The charge K‐region, Bay‐region, L‐region adjacent C(α)−C(β1) bond higher regions within molecule, these high RESP tends delocalize more strongly toward electron‐deficient radicals. Thus, activity N−C(α)−C(β1) region increased, supports proposed addition coupling PAA.

Language: Английский

Citations

4

Electrochemical Continuous-Flow Scholl Reaction toward Polycyclic Aromatic Hydrocarbons DOI
Weizhen Wang, Qiang Wang,

Xinglei He

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2243 - 2248

Published: March 8, 2024

The preparation of polycyclic aromatic hydrocarbons (PAHs) by the Scholl reaction is typically performed using superstoichiometric oxidants. Herein, we develop an electrochemical continuous-flow to access PAHs that features a reduction in use supporting electrolytes and easy scale-up without changing conditions setups. This allows synthesis distorted containing three [5]helicene units possess intriguing electronic optical properties.

Language: Английский

Citations

3

Access to indenofluorene skeletons via Pd-catalyzed sequential reaction involving cyclization of indenone–allenyne intermediates DOI
Shugao Zhu,

Hong Wang,

Shihan Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5884 - 5889

Published: Jan. 1, 2024

The rapid construction of 7,12-dihydroindeno[1,2- a ]fluorene skeletons is achieved via tandem palladium-catalyzed cross-coupling, Alder–ene isomerization and cyclization sequence from 1-(2-iodophenyl)-3-arylprop-2-yn-1-ones diynylic ethers.

Language: Английский

Citations

3

Construction of Multiply Arylated Fused Heterocycles through Rhodium-Catalyzed Double Annulation of Acylamido Arenes with Alkynes DOI

Mikishiro Hayashi,

Yoshinosuke Usuki, Tetsuya Satoh

et al.

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 123550 - 123550

Published: Feb. 1, 2025

Language: Английский

Citations

0

Electrocatalytic potential of bare and OH-functionalized co-N-doped pyrene for ORR and HER: A DFT study DOI

Angappan Kausalya,

Thangaraj Thiruppathiraja, Senthilkumar Lakshmipathi

et al.

Computational and Theoretical Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 115167 - 115167

Published: March 1, 2025

Language: Английский

Citations

0

Uniform Single-Domain Liquid Crystalline Hexagonal Rods by Synchronized Polymerization and Self-Assembly Using Disc-Shaped Monomers DOI
Minchao Li, Yuanxin Ma, Jing Li

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

The fabrication of nanostructures from polycyclic aromatic hydrocarbons (PAHs) is highly attractive owing to their unique optical, electrical, and magnetic properties. However, the creation uniform well-defined PAH by self-assembly still remains a significant challenge. Herein, we report that hexagonal rods can be obtained triphenylene (TP)-derived monomers synchronized polymerization (SPSA). These have single-domain columnar liquid crystalline structure in which columns formed stacked TPs are along long axis rods. length/diameter ratios tuned over wide range. Key factors achieve SPSA PAHs were analyzed, formation mechanism was clarified. In particular, it observed successful occurs below an upper critical temperature, could attributed insufficient microphase separation between side chains main should general principle for SPSA. Furthermore, demonstrate stacking TP units significantly promotes intersystem crossing singlet excited state triplet state, resulting simultaneous fluorescence phosphorescence emission at room temperature. This work may extended range regulate light

Language: Английский

Citations

0

Intramolecular and intermolecular benzannulation of arylethanone derivatives enabled by visible light-induced catalytic generation of tether-tunable distonic radical anions DOI

Zhiyou Yu,

Ziye Zhan,

Kang Fu

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel method enables inter-/intramolecular benzannulation to synthesize PAHs have been disclosed. Experimental and DFT data confirm the TDRA's role in HAA step of enolized 1,3-dicarbonyls via asynchronous PCET.

Language: Английский

Citations

0

Electrochemical Annulation of ortho‐Alkynylbiphenyls to Fused Sulfenyl Phenanthrenes and Spiro Cyclohexenone Indenes DOI
Anil Balajirao Dapkekar,

Jakkula Naveen,

Gedu Satyanarayana

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(1), P. 18 - 23

Published: Nov. 21, 2023

Abstract Here, we present an electrochemically induced synthesis of 9‐sulfenylarylphenanthrenes and 3’‐sulfenylarylspiro‐cyclohexa[4.5]trienones starting from o ‐alkynylbiphenyls diaryl disulfides. This method was accomplished through constant current electrolysis 10 mA in undivided cell setup by utilizing CH 3 CN as a solvent LiClO 4 electrolyte at room temperature. Notably, the strategy enabled formation sulfenylphenanthrenes sulfenyl spiro cyclohexa[4.5]trienones 70%–95% yield. Scale‐up synthesis, mechanistic studies, cyclic voltammetry have also been carried out.

Language: Английский

Citations

7