Photocatalyzed Aryl C‐H Fluorocarbonylation with CF2Br2 DOI

Kehan Zhou,

Yuheng Xiao,

Zhibin Huang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Abstract The use of abundant and inexpensive fluorine feedstocks to synthesize fluorinated compounds is a promising strategy that has not been extensively investigated. Dibromodifluoromethane (CF 2 Br ) an source rarely used for C−H fluoroalkylation. This study reveals iridium‐catalyzed, tunable synthesizing acyl fluorides difluorobromomethylated products using CF . To achieve the desired products, this process only requires change solvent (from DMSO 1,4‐dioxane) under blue LED illumination. A variety arenes heteroarenes with electron‐donating substituents were successfully used, yielding corresponding in moderate good yields. Mechanistic experiments revealed served dual role, functioning as both nucleophilic reagent fluorocarbonylation.

Language: Английский

Oxygen Migration–Defluorination Strategy Enables the Aminocarbonylation of Enaminones with o-Aminobenzamides and CF2Br2 DOI

Wanqing Zuo,

Renhua Zheng,

Yinghong Huang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 24, 2025

The development of different concept approaches and user-friendly carbonyl surrogates for aminocarbonylation is highly desirable. Herein, we report the photocatalytic enaminones with easily available o-aminobenzamides CF2Br2 through an oxygen migration-defluorination strategy. reaction features switchable transformation construction carbamoyl-substituted enol products allows expedient synthesis fully substituted maleimides under mild conditions.

Language: Английский

Citations

2

Pd‐Catalyzed Synthesis of Aryl Esters Involving Difluorocarbene Transfer Carbonylation DOI
Lu Wang,

Chengxian Hu,

Xue Yang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(10)

Published: Feb. 14, 2024

Abstract A Pd‐catalyzed three‐component intermolecular reaction between aryl halides, ClCF 2 COONa and phenols is developed. series of benzoates were synthesized in up to 84 % yield via difluorocarbene transfer carbonylation. It devoted acquiring the targeted products by construction new C−C, C=O C−O bonds a one‐pot, one‐step process. The feature this method includes use readily available starting materials, showing outstanding resistance spatial obstruction simple operation procedure with mild conditions. Therefore, makes methodology useful alternative other schemes typically used for synthesis esters.

Language: Английский

Citations

6

Base-controlled selective cleavage of the C–F bond of difluorocarbene for the divergent assembly of indolizines DOI
Chun‐Yan Wu, Xiang‐Long Chen, Dongsheng Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4214 - 4218

Published: Jan. 1, 2024

A [3 + 1 1] cascade annulation reaction for the divergent construction of trisubstituted indolizines using sulfoxonium ylides, BrCF 2 CO Me and pyridinium salts as readily available substrates has been developed.

Language: Английский

Citations

5

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

Rh-catalyzed double carbonylation of cyclopropenes toward valerolactone derivatives via cleavage of carbon–carbon double bonds DOI

Song‐Zhou Cai,

Can Li,

Suliang Wang

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

Language: Английский

Citations

0

Monodefluorinative Halogenation of Perfluoroalkyl Ketones via Organophosphorus-Mediated Selective C–F Activation DOI Creative Commons
Ha Eun Kim, Jun‐Ho Choi, Won‐jin Chung

et al.

JACS Au, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Through the prosperity of organofluorine chemistry in modern organic synthesis, perfluorinated compounds are now abundant and widely available. Consequently, these substances become attractive starting materials for production complex, multifunctional fluorinated molecules. However, inherent challenges associated with activation discrimination C–F bonds typically lead to overdefluorination as well functional group incompatibility. To address problems, our utilized a rationally designed organophosphorus reagent that promoted mild selective manipulation single bond trifluoromethyl pentafluoroethyl ketones via an interrupted Perkow-type reaction, which allowed replacement fluorine more labile synthetically versatile congeners such chlorine, bromine, iodine. The resulting α-haloperfluoroketones have two reactive units orthogonal properties would be suitable subsequent structural diversification. DFT calculations identified favorable P–F interaction crucial factor from both thermodynamic kinetic viewpoints.

Language: Английский

Citations

0

Research Progress on Carbonylation Involving Name Reactions DOI
Yaowei Wang, Peng Wang,

Huibing Shi

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(1), P. 104 - 104

Published: Jan. 1, 2025

Language: Английский

Citations

0

Palladium‐Catalyzed Carbonylative Sonogashira Transformations: Advancements and Insights DOI Open Access

P Vishnu,

Padinjare Veetil Saranya,

Gopinathan Anilkumar

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Abstract Palladium‐catalyzed carbonylative reactions, used as a tool for the insertion of carbonyl group into organic moieties, is synthetically useful transformation. Carbonylative Sonogashira coupling convenient approach synthesis α,β‐acetylenic ketones which are important class molecules in pharmaceutical and industrial fields. Development greener approaches environmentally benign catalytic systems put forward enormous opportunities this field moreover, these researches indicate formation heterocycles via carbonylation strategy, major highlight. Herein, we discuss progress achieved palladium‐catalyzed from 2013 to 2024 its future prospects.

Language: Английский

Citations

0

Palladium-catalyzed Narasaka–Heck carbonylation for the construction of functionalized ynones DOI
Ming Li, Fei Yang,

Shan-Mei Xu

et al.

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

Published: Jan. 1, 2025

Pd-catalyzed Narasaka–Heck carbonylation efficiently synthesizes functionalized alkynones (70% yield) under mild conditions. This strategy offers a multifunctional platform for bioactive molecule construction in medicinal chemistry.

Language: Английский

Citations

0

Switching from gem-difluorovinylation to carboxylation: ligand-enabled palladium-catalyzed Heck annulation of alkene-tethered aryl halides with sodium difluorochloroacetate DOI
Yu Xia, Wenqi Li,

Minzhu Wei

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3491 - 3496

Published: Jan. 1, 2024

The use of a ligand to tune palladium-catalyzed intramolecular Heck gem -difluorovinylation and carboxylation is reported. Sodium difluorochloroacetate (ClCF 2 COONa) acts as both difluorocarbene (:CF ) carboxyl source.

Language: Английский

Citations

2