Photocatalyzed Aryl C‐H Fluorocarbonylation with CF2Br2 DOI

Kehan Zhou,

Yuheng Xiao,

Zhibin Huang

и другие.

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Сен. 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.

Язык: Английский

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

Wanqing Zuo,

Renhua Zheng,

Yinghong Huang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 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.

Язык: Английский

Процитировано

6

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

Song‐Zhou Cai,

Can Li,

Suliang Wang

и другие.

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 25, 2025

Язык: Английский

Процитировано

1

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

Chengxian Hu,

Xue Yang

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(10)

Опубликована: Фев. 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.

Язык: Английский

Процитировано

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4214 - 4218

Опубликована: Янв. 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.

Язык: Английский

Процитировано

5

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

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(12), С. 3491 - 3496

Опубликована: Янв. 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.

Язык: Английский

Процитировано

3

Palladium-catalyzed difluorocarbene transfer enables access to enantioenriched chiral spirooxindoles DOI Creative Commons
Zhiwen Nie,

Keqin Wu,

Xiaohang Zhan

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Окт. 1, 2024

Язык: Английский

Процитировано

3

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

и другие.

JACS Au, Год журнала: 2025, Номер unknown

Опубликована: Янв. 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.

Язык: Английский

Процитировано

0

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

Huibing Shi

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(1), С. 104 - 104

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

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

P Vishnu,

Padinjare Veetil Saranya,

Gopinathan Anilkumar

и другие.

The Chemical Record, Год журнала: 2025, Номер unknown

Опубликована: Март 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.

Язык: Английский

Процитировано

0