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

и другие.

Journal of Molecular Modeling, Год журнала: 2024, Номер 30(6)

Опубликована: Май 24, 2024

Язык: Английский

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

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 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.

Язык: Английский

Процитировано

1
Palladium-Catalyzed Three-Component Cascade Carbonylation Reaction to Construct Benzofuran Derivatives DOI
Ming Li,

Shan-Mei Xu,

Dong‐Ping Chen

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7741 - 7746

Опубликована: Май 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.

Язык: Английский

Процитировано

6
Nickel-Catalyzed Narasaka–Heck Cyclization Carbonylation of Unsaturated Oxime Esters with Arylboronic Acids DOI
Ming Li,

Fan Gao,

Shan-Mei Xu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7834 - 7840

Опубликована: Сен. 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

Язык: Английский

Процитировано

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

Mingxia Wu

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(21), С. 4509 - 4514

Опубликована: Авг. 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.

Язык: Английский

Процитировано

2
Recent Progress in Metal-Catalyzed C(sp³)-P Bond Formation DOI
Jia‐Lin Tu, Zhengjia Shen, Binbin Huang

и другие.

Tetrahedron, Год журнала: 2024, Номер 168, С. 134352 - 134352

Опубликована: Ноя. 1, 2024

Язык: Английский

Процитировано

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(20), С. 5144 - 5150

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

Yaru Fang,

Mingruo Ding,

Xueliang Huang

и другие.

ChemCatChem, Год журнала: 2023, Номер 16(5)

Опубликована: Ноя. 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.

Язык: Английский

Процитировано

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

Ran Song

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(7), С. 2015 - 2020

Опубликована: Янв. 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.

Язык: Английский

Процитировано

0
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

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Март 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.

Язык: Английский

Процитировано

0