Magnetically Retractable Tea Extract Stabilized Palladium Nanoparticles for Denitrogenative Cross-Coupling of Aryl Bromides with Arylhydrazines Under Green Conditions: An Alternate Route for the Biaryls Synthesis DOI
Sumanth Hegde, Aatika Nizam

Published: Jan. 1, 2023

This study describes the synthesis of palladium nanoparticles stabilized from tea extracts supported on magnetic and named as ION-SiO2/TE-Pd(0). In this respect, while our is one limited number studies reported for catalytic denitrogenative coupling arylbromide arylhydrazine. lead to construction important substituted biaryls easily accessible bromoarenes bearing various substituents with 82-92% yields. The synthesized nanocatalyst were characterized using structural morphological characterization techniques. It was also observed that ION-SiO2/TE-Pd(0) catalyst had good activity even after six cycles.

Language: Английский

Recent advances in sustainable N-heterocyclic carbene-Pd(II)-pyridine (PEPPSI) catalysts: A review DOI

Govardhana Reddy Peddiahgari Vasu,

Krishna Reddy Motakatla Venkata,

Kakarla Raghava Reddy

et al.

Environmental Research, Journal Year: 2023, Volume and Issue: 225, P. 115515 - 115515

Published: Feb. 24, 2023

Language: Английский

Citations

29
Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes† DOI
Pui Ying Choy, Kin Boon Gan, Fuk Yee Kwong

et al.

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 41(9), P. 1099 - 1118

Published: Dec. 13, 2022

Comprehensive Summary Sonogashira cross‐coupling protocol, typically showing the reaction between aryl/vinyl halide and terminal alkyne, has been a widely used protocol for constructing C(sp 2 )‐C(sp) bond. The resulting internal alkynes are highly versatile reaching differently functionalized alkyne‐containing scaffolds or serving as valuable synthetic synthons to many other functional groups. It is worth noting that products originated from this coupling mostly applicable be transformed into corresponding Z ‐alkene, alkane, heterocyclic moieties in natural product syntheses. conditions catalyst systems able tweaked order facilitate activation of steric hindered and/or electron‐rich electrophiles. Pd‐catalyzed copper‐free caught increasing attention improved method can more environmentally friendly. What more, readily amended allow fusion carbonylation decarboxylation step catalytic cycle, thus complex yet convergent synthesis proceed an operationally simple one‐pot manner.

Language: Английский

Citations

33
Magnetically retractable tea extract stabilized palladium nanoparticles for denitrogenative cross-coupling of aryl bromides with arylhydrazines under green conditions: An alternate route for the biaryls synthesis DOI Creative Commons
Sumanth Hegde, Aatika Nizam

Catalysis Communications, Journal Year: 2024, Volume and Issue: 187, P. 106862 - 106862

Published: Feb. 1, 2024

Novel palladium based magnetic nanocatalyst was synthesized by the co-precipitation method and coated with silica tea extract as stabilizing agent. Palladation onto prepared nanocomposite done to get ION-SiO2/TE-Pd(0) catalyst. Our study is one of limited number studies reported for catalytic denitrogenative coupling arylbromide arylhydrazine. This led construction important substituted biaryls bearing various substituents 82–92% yields. The characterized using structural morphological characterization techniques. It also observed that only 2 mol% catalyst sufficient catalysis reusable upto six cycles.

Language: Английский

Citations

8
Suzuki–Miyaura Cross-Coupling of 2-Pyridyl Trimethylammonium Salts by N–C Activation Catalyzed by Air- and Moisture-Stable Pd–NHC Precatalysts: Application to the Discovery of Agrochemicals DOI

Yuge Hu,

Yanqing Gao,

Jiuhui Ye

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(17), P. 2975 - 2980

Published: April 20, 2023

We report the first Suzuki-Miyaura cross-coupling of 2-pyridyl ammonium salts by highly selective N-C activation catalyzed air- and moisture-stable Pd(II)-NHC (NHC = N-heterocyclic carbene) precatalysts. The use well-defined reactive [Pd(IPr)(3-CF3-An)Cl2] (An aniline) or [Pd(IPr)(cin)Cl] (cin cinnamyl) catalysts permits an exceptionally broad scope to furnish valuable biaryl heterobiarylpyridines that are ubiquitous in medicinal chemistry agrochemistry research. overall process leverages Chichibabin C-H amination pyridines with enable attractive strategy problem. utility method discovery potent agrochemicals is presented. Considering importance 2-pyridines versatility methods, we envision this new C-H/N-C will find application.

Language: Английский

Citations

10
Copper(I)–Thiazol-2-ylidenes: Highly Reactive N-Heterocyclic Carbenes for the Hydroboration of Terminal and Internal Alkynes. Ligand Development, Synthetic Utility, and Mechanistic Studies DOI
Jin Zhang, Xue Li, Tao Li

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(24), P. 15323 - 15333

Published: Nov. 30, 2022

In the last 15 years, copper-catalyzed borylative transformations utilizing boryl–copper have been established as a powerful activation mode in organic synthesis and catalysis, enabling direct of various π-systems. Although many these use NHC (N-heterocyclic carbene) ligands, studies almost exclusively limited to derivatives imidazol-2-ylidenes. However, molecular properties N-aryl-imidazol-2-ylidenes, such IPr (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), are by (1) high degree heteroatom stabilization (2) symmetrical substitution nitrogen atoms. Herein, we report study on Cu(I)–thiazol-2-ylidenes, thiazole analogues imidazol-2-ylidenes, which feature distinct half-umbrella shape coordinating ligand exhibit lower ancillary through reduced π-donation from sulfur. We present development family stable where combined sterics thiazol-2-ylidenes lead monomers [Cu(NHC)X] or bridged-halo dimers [Cu(NHC) (μ-X)]2, their crystallographic characteristics, application hydroboration alkynes afford trisubstituted vinylboronates β-hydroboration internal terminal alkynes. Application late-stage modification detailed mechanistic catalyst structure presented. Most crucially, Cu(I)–thiazol-2-ylidenes show much higher β-selectivity than that classical affording vinylborons excellent yields at ambient conditions. The unique "half-umbrella" reverses α/β regioselectivity observed with imidazol-2-ylidenes Kinetic demonstrate supersede Considering significant utility π-systems, anticipate will advance synthetic catalysis.

Language: Английский

Citations

13
Synthesis and a combined experimental/theoretical structural study of a comprehensive set of Pd/NHC complexes witho-,m-, andp-halogen-substituted aryl groups (X = F, Cl, Br, CF3) DOI
Roman O. Pankov, Darya O. Prima, Alexander Yu. Kostyukovich

et al.

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(13), P. 4122 - 4135

Published: Jan. 1, 2023

Pd/NHC complexes (NHCs - N-heterocyclic carbenes) with electron-withdrawing halogen groups were prepared by developing an optimized synthetic procedure to access imidazolium salts and the corresponding metal complexes. Structural X-ray analysis computational studies have been carried out evaluate effect of CF3 substituents on Pd-NHC bond provided insight into possible electronic effects molecular structure. The introduction changes ratio σ-/π-contributions but does not affect energy. Here, we report first approach a comprehensive range o-, m-, p-XC6H4-substituted NHC ligands, including incorporation Pd (X = F, Cl, Br, CF3). catalytic activity obtained was compared in Mizoroki-Heck reaction. For substitution atoms, following relative trend observed: X Br > F for all changed order: m-X, p-X o-X. Evaluation showed significant increase catalyst performance case unsubstituted complex.

Language: Английский

Citations

7
Atomically precise nanocluster-catalyzed coupling reactions DOI
Jinhui Hu, Yiming Li, Bei Zhang

et al.

Inorganic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(16), P. 4974 - 5003

Published: Jan. 1, 2024

This review highlights the factors that can dictate properties of cluster-based catalysts towards coupling reactions, such as ligand effect, doping support and defective effect.

Language: Английский

Citations

2
Tetrabutylammonium Bromide (TBAB)-Promoted, Pd/Cu-Catalyzed Sonogashira Coupling of N-Tosyl Aryltriazenes DOI
Jun Cao,

Wenbin Ding,

Gang Zou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4576 - 4580

Published: May 22, 2024

Sonogashira coupling of

Language: Английский

Citations

1
Encapsulation of TixFeyLamOz nanoparticles into NH2-MIL-125(Ti) to fabricate a promising photocatalyst for the C–N coupling reaction DOI
Yahya Absalan,

Mohammad Rafsanjani Dehghazi,

Реза Самавати

et al.

Reaction Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 9(4), P. 849 - 860

Published: Jan. 1, 2024

An array of organic compounds and natural products can be synthesized through carbon–nitrogen coupling reactions.

Language: Английский

Citations

1
Synthesis of α-Substituted Alkenylammonium Salts through Suzuki–Miyaura and Sonogashira Coupling DOI

Aoi Yoshita,

Yota Sakakibara, Kei Murakami

et al.

Bulletin of the Chemical Society of Japan, Journal Year: 2023, Volume and Issue: 96(3), P. 303 - 305

Published: Feb. 24, 2023

Abstract Alkenylammonium salts are a unique class of compounds, wherein an electron-withdrawing ammonio group is attached to olefin. Although these structurally simple, the synthesis α-substituted alkenylammonium has been sparsely explored. Herein we report α-aryl and α-alkynylated through Suzuki–Miyaura Sonogashira coupling.

Language: Английский

Citations

3