Mechanistic insights into C(sp2)-H activation in 1-Phenyl-4-vinyl-1H-1,2,3-triazole derivatives: a theoretical study with palladium acetate catalyst DOI
Wagner F. Fogos, Milena D. Lessa, Fernando de Carvalho da Silva

et al.

Journal of Molecular Modeling, Journal Year: 2024, Volume and Issue: 30(6)

Published: May 24, 2024

Language: Английский

Palladium-Catalyzed Three-Component Cascade Carbonylation Reaction to Construct Benzofuran Derivatives DOI
Ming Li,

Shan-Mei Xu,

Dong‐Ping Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7741 - 7746

Published: May 14, 2024

A novel three-component cyclization carbonylation reaction of iodoarene-tethered propargyl ethers with amine and CO is reported. This palladium-catalyzed cascade undergoes a sequence oxidative addition, unsaturated bond migration, carbonyl insertion, nucleophilic attack to deliver the benzofuran skeleton. Both aromatic amines aliphatic could proceed smoothly in this transformation under one atm CO.

Language: Английский

Citations

4
Nickel-Catalyzed Narasaka–Heck Cyclization Carbonylation of Unsaturated Oxime Esters with Arylboronic Acids DOI
Ming Li,

Fan Gao,

Shan-Mei Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7834 - 7840

Published: Sept. 5, 2024

The Narasaka-Heck reaction is one of the most straightforward methods for constructing pyrroline derivatives. Herein, we report a novel nickel-catalyzed three-component carbonylation reaction, which cleverly realizes continuous construction C(sp

Language: Английский

Citations

4
Palladium-catalyzed intermolecular formal [3+2] cyclization/C-H alkylation of polyfluoroarenes DOI
Zhongyao Jiang, Chenglin Liu,

Mingxia Wu

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A sequential three-component intermolecular carbopalladation/Heck cyclization/intermolecular C–H bond functionalization for versatile alkylated polyfluoroarenes containing an indene skeleton is presented.

Language: Английский

Citations

0
Palladium‐Catalyzed Carbonylation of ortho‐Alkenyl Iodobenzenes for the Construction of 3‐Arylindenones DOI Open Access
Min Qian, Lingyun Yao, Zhi Li

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 14, 2025

Comprehensive Summary We developed a novel Pd‐catalyzed carbonylation of ortho ‐alkenyl iodobenzenes with CO, affording diverse array 3‐arylindenones in good to excellent yields (up 94% yield). This methodology exhibits broad substrate scope and functional group compatibility. The synthetic utility was demonstrated by gram‐scale reaction, product derivatizations, the preparation an intermediate for PPARγ agonist.

Language: Английский

Citations

0
Stereoselective Construction of Trisubstituted 1,3‐Enynes <i>via</i> Aryl to Vinyl 1,4‐Palladium Migration DOI Open Access
Jie Lin, Juan Ma, Liandi Wang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4509 - 4514

Published: Aug. 2, 2024

Abstract Palladium‐catalyzed stereoselective olefinic C−H alkynylation of gem ‐diarylsubstituted ethylenes with propargylic alcohols was achieved to access diverse unsymmetrical 1,3‐enynes. The regio‐ and stereoselectivities were established through a 1,4‐palladium migration from aryl vinyl in the presence 2‐FC 6 H 4 OH as additive. Mechanistic investigations suggest that cleavage bond might not be involved rate‐determining step catalytic process.

Language: Английский

Citations

2
Regioselective polyfluoroarylation of alkenyl C–H bonds via aryl to vinyl 1,4-palladium migration DOI
Jie Lin, Juan Ma, Liandi Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5144 - 5150

Published: Jan. 1, 2023

Efficient palladium-catalyzed regioselective vinylic C–H polyfluoroarylation of gem -disubstituted ethylenes with polyfluoroarenes was realized via an aryl to vinyl 1,4-palladium migration process access various polyfluorinated triarylethenes.

Language: Английский

Citations

5
Taming the Selective C−H Bond Activation through 1,5‐Palladium Migration DOI

Yaru Fang,

Mingruo Ding,

Xueliang Huang

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 16(5)

Published: Nov. 29, 2023

Abstract “Through space” metal/hydrogen shift constitutes one of the efficient elementary step in organometallic chemistry to achieve selective remote C−H bond functionalization. Compared with relatively extensive exploration on 1,4‐palladium migration, processes corresponding 1,5‐palladium translocation are far less explored. Based our understanding related research areas, we summarized advances achieved activation through a key migration this minireview. The background, reaction scope, and more importantly, mechanistic rationale each transformation was discussed. We hope by reading minireview, could get general perspective direct via 1,5‐palladium/hydrogen shift, understand why such process is common when compared going 1,4‐palladium/hydrogen eventually be inspired develop practical ways for synthesis valuable molecules, which not prepared easily other traditional approaches.

Language: Английский

Citations

4
Recent Progress in Metal-Catalyzed C(sp³)-P Bond Formation DOI
Jia‐Lin Tu, Zhengjia Shen, Binbin Huang

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 168, P. 134352 - 134352

Published: Nov. 1, 2024

Language: Английский

Citations

1
Mechanistic insights into C(sp2)-H activation in 1-Phenyl-4-vinyl-1H-1,2,3-triazole derivatives: a theoretical study with palladium acetate catalyst DOI Creative Commons
Wagner F. Fogos, Milena D. Lessa, Fernando Carvalho da Silva

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: March 13, 2024

Abstract Context The activation of C-H bonds is a fundamental process in synthetic organic chemistry, which enables their replacement by highly reactive functional groups. Coordination compounds serve as effective catalysts for this purpose, they facilitate chemical transformations interacting with bonds. A comprehensive understanding the mechanism type bond lays foundation development efficient protocols cross-coupling reactions. We explored C(sp2)-H 1-Phenyl-4-vinyl-1H-1,2,3-triazole derivatives CH3, OCH3 and NO2 substituents para position phenyl ring, using palladium acetate catalyst. studied reaction first step subsequent conjugation triazoles naphthoquinones Heck-type to create C-C bond. basic nitrogen atoms 1,2,3-triazole coordinate preferentially cationic center form an activated species. concerted proton transfer from terminal vinyl carbon one ligands low energy main activation. This study offers significant mechanistic insights enhancing effectiveness synthesis. Methods All calculations were performed Gaussian 09 software package density theory (DFT). structures all path components fully optimized CAM-B3LYP Def2-SVP basis set. geometries analyzed computing second-order Hessian matrix confirm whether corresponding structure minimum or true transition state. To account solvent effects, Polarizable Continuum Model Integral Equation Formalism (IEFPCM) water was used.

Language: Английский

Citations

0
Phenol-mediated decarboxylative proton transfer of γ-methylidene-δ-valerolactones: an approach towards (E)-2,4-pentadienoates DOI

Feng Wei,

Xiaoying Wu,

Ran Song

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2015 - 2020

Published: Jan. 1, 2024

A phenol-mediated decarboxylative proton transfer of γ-methylidene-δ-valerolactones (GMDVs) was developed, affording the target polysubstituted ( E )-2,4-pentadienoates in 99% yields with / Z up to 99 : 1.

Language: Английский

Citations

0