Electrochemical Rhodium-Catalyzed C–H Cyclodimerization of Alkynes to Access Diverse Functionalized Naphthalenes: Involvement of RhIV/V and RhI Dual Catalysis DOI

Ziyi Guo,

Junjie Zhang, Jitan Zhang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(42), P. 7784 - 7789

Published: Oct. 17, 2022

The first electrochemical rhodium-catalyzed C-H cyclodimerization of alkynes for the direct construction functionalized naphthalenes was reported. practicality and synthetic value this strategy were demonstrated by readily accessible scale-up synthesis transformation products. Detailed mechanistic studies evidenced that electricity played an important role during disproportionation (ECD) process to generate maintain catalytically active RhIV/V RhI species, which conducted activation.

Language: Английский

Electrochemically enabled rhodium-catalyzed [4 + 2] annulations of arenes with alkynes DOI
Zi-Chen Wang,

Rui-Tao Li,

Ma Qiang

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(23), P. 9515 - 9522

Published: Jan. 1, 2021

Herein, electrochemically driven, Rh( iii )-catalyzed regioselective annulations of arenes with alkynes have been established.

Language: Английский

Citations

23
Rhoda‐Electrocatalyzed C−H Methylation and Paired Electrocatalyzed C−H Ethylation and Propylation DOI
Krzysztof Kuciński, Hendrik Simon, Lutz Ackermann

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 28(1)

Published: Oct. 29, 2021

The use of electricity over traditional stoichiometric oxidants is a promising strategy for sustainable molecular assembly. Herein, we describe the rhoda-electrocatalyzed C-H activation/alkylation several N-heteroarenes. This catalytic approach has been successfully applied to arenes, including biologically relevant purines, diazepam, and amino acids. versatile alkylation featured water as co-solvent user-friendly trifluoroborates alkylating agents. Finally, rhoda-electrocatalysis with unsaturated organotrifluoroborates proceeded by paired electrolysis.

Language: Английский

Citations

21
Electrooxidative iridium-catalyzed sp2 C−H activation-annulation leading to cationic π-extended heteroaromatics DOI
Qi‐Liang Yang, Nana Guo,

Shu-Xian Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4849 - 4856

Published: Jan. 1, 2024

An electrochemically driven, Cp*Ir( iii )-catalyzed method for alkenyl and aromatic C(sp 2 )–H activation coupling with alkynes the synthesis of biologically useful quaternary ammonium salts under mild conditions is demonstrated.

Language: Английский

Citations

3
C–H Acyloxylation of Polycyclic Aromatic Hydrocarbons DOI
Yota Sakakibara, Kei Murakami, Kenichiro Itami

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(2), P. 602 - 607

Published: Jan. 7, 2022

The C-H acyloxylation of polycyclic aromatic hydrocarbons (PAHs) is described. This reaction constructs aryl acyloxylate scaffolds from PAHs with equimolar hypervalent iodine compounds under mild conditions. Interestingly, the blue light irradiation accelerated this transformation. Additionally, synthesis structurally new symmetric and unsymmetric diaroyloxylated fluoranthenes was accomplished a ruthenium photoredox catalyst.

Language: Английский

Citations

14
Multidimensional Screening Accelerates the Discovery of Rhodium Catalyst Systems for Selective Intra- and Intermolecular C–H Amidations DOI
Jiwoo Jeong, Hoimin Jung, Dongwook Kim

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(13), P. 8127 - 8138

Published: June 23, 2022

We report herein a series of tailored CpXRh(LX)Cl catalyst systems for the outer-sphere C–H amidations discovered by high-throughput experimentation. Using diverse repertoire Cp-tunable group 9 [CpXMCl2]2 precatalysts in combination with bidentate LX-type co-ligands, we have established premixing protocol fast and convenient situ generation an array half-sandwich metal complexes. Benefitting from designed multidimensional approach to simultaneously screen center, CpX, nitrene precursors, optimal CpXRh(III)(LX) catalysts were quickly identified intra- intermolecular also enantioselective transformation using N-tosyloxycarbamates as nitrenoid precursor.

Language: Английский

Citations

13
Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C–H/N–H coupling for the synthesis of N–H indoles DOI

Youyoung Kim,

Dongwook Kim, Sukbok Chang

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(92), P. 12309 - 12312

Published: Jan. 1, 2021

Herein, an iridium(III)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis a variety 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that reaction proceeds through electro-oxidation induced reductive elimination pathway.

Language: Английский

Citations

16
Mechanistic insights into facilitating reductive elimination from Ni(ii) species DOI

Bolin Qiao,

Fa-You Lin,

Dongmin Fu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(62), P. 8008 - 8019

Published: Jan. 1, 2024

Reductive elimination is a key step in Ni-catalysed cross-couplings, which often considered to result new covalent bonds. Due the weak oxidizing ability of Ni(II) species, reductive eliminations from centers are challenging. A thorough mechanistic understanding this process could inspire rational design coupling reactions. In article, we give an overview recent advances study species achieved by our group. Three possible models for were investigated and discussed, including direct elimination, electron density-controlled oxidation-induced elimination. Notably, requires high activation energy some cases. contrast, pathways can significantly enhance driving force accelerating formation The intricate reaction mechanisms each these thoroughly discussed systematically summarized paper. These computational studies showcase characteristics three hope that it will spur development cross-coupling

Language: Английский

Citations

2
Electrochemical C3 acyloxylation reactions of 2H-indazoles with carboxylic acids via C(sp2)–O coupling DOI
Xin Liu,

Yibin Hu,

Yuanbin She

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 8117 - 8123

Published: Jan. 1, 2023

The electrochemical C3 acyloxylation reactions of 2 H -indazoles with carboxylic acids in the presence K CO 3 were successfully developed, which green and sustainable without transition-metal catalysts stoichiometric oxidants.

Language: Английский

Citations

6
Electrochemical ruthenium-catalysed C–H activation in water through heterogenization of a molecular catalyst DOI Creative Commons
Jan Bühler, Jonas Zurflüh, Sebastian Siol

et al.

Catalysis Science & Technology, Journal Year: 2022, Volume and Issue: 12(5), P. 1512 - 1519

Published: Jan. 1, 2022

The synthesis and characterisation of an immobilised molecular ruthenium catalyst for the selective oxidation organic substrates in fully aqueous media with high selectivity over competing oxygen evolution reaction is reported.

Language: Английский

Citations

9
Ruthenium(II)-Catalyzed Sterically Hindered C–H Acyloxylation to Synthesize Biaryl Isoquinoline Derivatives via Peresters DOI
Hao Liu,

Wei Chi,

Lin Dong

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 3148 - 3158

Published: Feb. 22, 2023

A novel C-H acyloxylation method of 1-(1-naphthalen-1-yl)isoquinoline derivatives with peresters in the presence [Ru(p-cymene)Cl2]2 has been developed. The combination ruthenium(II), AgBF4, CoI2, and 2,2,6,6-tetramethyl-1-piperidinyloxy is found to be an effective catalytic system provide various biaryl compounds satisfactory yields within minutes. Notably, steric hindrance a very important determinant reaction.

Language: Английский

Citations

5