Electrochemical Aminotrifluromethylation of Unactivated Alkenes with Langlois’ Reagent as the CF3 Source DOI

Tongshun An,

Xiaowen Qin, Chenwei Liu

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 48(5), С. 2183 - 2187

Опубликована: Дек. 26, 2023

An electrochemical approach for synthesizing various trifluoromethylated pyrrolidines was developed by utilizing Langlois’ reagent as the CF 3 source, and different unactivated alkenes can be converted to corresponding heterocycles in 43–80% yields.

Язык: Английский

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents DOI Creative Commons
Akira Yoshimura, Viktor V. Zhdankin

Chemical Reviews, Год журнала: 2024, Номер unknown

Опубликована: Сен. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Язык: Английский

Процитировано

34

Electrochemical oxidative CF3 radical-induced lactonization and etherification of terminal and internal alkenes DOI Creative Commons

Riccardo Grigolato,

Tommaso Fantoni,

Giuseppe Autuori

и другие.

RSC Advances, Год журнала: 2025, Номер 15(19), С. 15302 - 15309

Опубликована: Янв. 1, 2025

Introducing CF 3 groups boosts drug properties by enhancing metabolic stability and bioavailability. This study reports an electrochemical oxidative difunctionalization of flexible alkenes to form -substituted lactones cyclic ethers.

Язык: Английский

Процитировано

0

Visible‐Light‐Catalyzed Formal [3+2] Annulation‐Aromatization of Amidines with Isoquinolinium N‐Ylides: Access to Imidazo[2,1‐a]isoquinolines DOI Open Access
Lvyin Zheng,

Xiaoying Zou,

Xiaojuan Yang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(21), С. 3629 - 3636

Опубликована: Сен. 21, 2023

Abstract A visible‐light‐catalyzed formal [3+2] annulation‐aromatization reaction for the synthesis of various substituted imidazo[2,1‐ a ]isoquinolines from amidines with stabilized isoquinolinium N ‐ylides in presence bases is developed. The procedure reported here involves direct C−H activation and formation C−C/C−N bonds one‐pot. mechanism probed by radical‐trapping experiment, fluorescence quenching, light on/off experiments. late‐stage modification experiments provide potential applications field organic medicinal chemistry chemists.

Язык: Английский

Процитировано

7

Palladium–Copper-Catalyzed Oxidative Intermolecular [2 + 2 + 2] Coupling–Annulation: Regioselective Synthesis of Multiaryl-Substituted Benzenes DOI
Yihan Wang,

Beining Yang,

Bo Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4579 - 4594

Опубликована: Март 20, 2024

A palladium-catalyzed intermolecular [2 + 2 2] oxidative coupling–annulation of terminal alkenes and alkynes using copper(II) as the oxidant has been developed through direct C–C bond formation. These reactions provide effective access to multiaryl-substituted benzenes with high regioselectivity in absence any ligands. The features this protocol are broad substrate scope, atom step economy. aggregation-induced emission properties selected products were further investigated. synthesized may be worth exploring for applications fields advanced functional materials or drugs.

Язык: Английский

Процитировано

2

Synthesis of Primary and Secondary Amines via Electrochemical Reduction of Hydrazines DOI

Dong Wang,

Qiulu Wang,

Mingxia Liu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(51), С. 11123 - 11128

Опубликована: Дек. 13, 2024

We herein introduce an electrochemical route for the N–N bond cleavage of hydrazines. This mild and green methodology utilized readily available mono- 1,1-disubstituted hydrazines or their HCl salts as starting materials to access a broad scope primary secondary amines in high yields. The mechanistic investigation suggests that amine product is formed by consecutive SET reduction, utilization hydrazine salt important providing sufficient conductivity acidity facilitate this reaction.

Язык: Английский

Процитировано

2

An aerobic copper-catalyzed multi-component reaction strategy for N′,N′-diaryl acylhydrazine synthesis: reactions and mechanism DOI

Lei Deng,

Wei Guo,

Xiaojuan Yang

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(4), С. 1132 - 1139

Опубликована: Дек. 20, 2023

A sequential multi-component reaction of aldehydes and aryl hydrazines for the synthesis N' , -diaryl acylhydrazines with high regioselectivity has been achieved via an aerobic copper-catalyzed process.

Язык: Английский

Процитировано

4

Visible Light Mediated Chemoselective Hydroxylation of Benzylic Methylenes DOI
Zhiyong Tan,

Tingting Chen,

Jinbin Zhu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2656 - 2664

Опубликована: Фев. 7, 2024

We have developed a metal-free photocatalytic selective hydroxylation of benzylic methylenes to secondary alcohols. This approach utilizes low-cost eosin Y as photocatalyst, O2 green oxidant, and inexpensive triethylamine inhibitor for overoxidation. The mild reaction conditions enable the production alcohols with 56–95% yields, making it promising environmental-friendly method synthesis from methylenes.

Язык: Английский

Процитировано

1

Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles DOI
Zhiying Zhang,

Yinyin Li,

Yatang Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16809 - 16827

Опубликована: Ноя. 1, 2024

A photocatalytic three-component cascade reaction of readily available enaminones, hydrazines, and CBr4 for the synthesis bromo-substituted pyrazoles in one pot has been demonstrated. This strategy involves intermolecular C-N/C-Br bond formation represents an efficient approach to construction 4-bromo-substituted with high regioselectivity, broad substrate scope, good functional group tolerance, convenient operation, mild conditions. Mechanistic investigations show that this proceeds via cyclization enaminones followed by a regioselective bromination using as "Br" source.

Язык: Английский

Процитировано

1

Recent applications of phenyl hydrazine in photoinduced chemical transformations DOI

Sangita Yadav,

Rohit Kumar, Vishal Srivastava

и другие.

Synthetic Communications, Год журнала: 2024, Номер unknown, С. 1 - 23

Опубликована: Дек. 3, 2024

Phenyl hydrazine has attracted attention in photoredox catalytic synthetic strategies for the formation of carbon-carbon (C-C) bond and Carbon-Heteroatom (C-N, C = N, C-P, C-S, S-N) bonds, because low cost ease availability make it a promising alternative method typical transition metal complex-based photocatalyzed synthesis. In this review, we have focused on recent radical coupling ­reactions phenyl via photochemical to form carbon–carbon carbon–heteroatom (N, P, S) bonds along with mechanism involved their reaction.

Язык: Английский

Процитировано

1

Overview of Phenylhydrazine‐Based Organic Transformations DOI Open Access
Pragati Kushwaha,

Ayush Bhardwaj,

Rashi

и другие.

ChemistrySelect, Год журнала: 2024, Номер 10(1)

Опубликована: Дек. 30, 2024

Abstract Phenylhydrazines, comprised of a phenyl group attached with hydrazine unit, contribute potentially to organic synthetic transformations. Because the myriad applications, last decade has witnessed considerable upsurge interest perform various reactions catalyzed/mediated/promoted by phenylhydrazines. Some these have shown high regioselectivity in short reaction time under mild conditions. The emergence innumerable transformations utilizing phenylhydrazine unleashed numerous openings for development diverse heterocyclic scaffolds. Given importance this valuable chemical entity, review highlights methodologies Moreover, present article will considerably synthesis as well pharmaceutical chemistry. Academically, be interesting and informative researchers attempting develop new routes structures.

Язык: Английский

Процитировано

0