Electrochemical Conversion of N‐Sulfinylamines to Sulfonimidoyl Fluorides DOI Open Access

Fang‐Ling Gao,

Xinglei He,

Bin Zhao

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 26, 2024

Comprehensive Summary The invention of novel linkers is a long‐lasting task in the area sulfur(VI) fluoride exchange reaction (SuFEx). Compared with most frequently investigated sulfonyl fluorides, synthetic accessibility toward its mono‐aza isostere, i.e. , sulfonimidoyl fluorides still limited. Herein, we report an electrochemical carbonfluorination readily available N ‐sulfinylamines to access various aryl and alkyl fluorides. transformation characterized by ready availability starting materials, mild conditions, obviating metal catalysts chemical oxidants.

Язык: Английский

Copper-Mediated Radical Fluorine-Atom Transfer to Sulfonyl Radical: A Dramatic 4-Methoxypyridine 1-Oxide Ligand Effect DOI
Hongwei Zhang, Xiaoxiao Sun,

Cheng Ma

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(5), С. 3115 - 3127

Опубликована: Фев. 13, 2024

Although the transition metal-catalyzed radical fluorine atom transfer (FAT) strategy has emerged as a powerful tool for construction of C–F bonds, to our knowledge, this approach rarely been applied formation S–F bonds. Here, we report that 4-methoxypyridine 1-oxide can serve an inexpensive and simple yet effective ligand thus promote transformation copper-mediated challengeable FAT sulfonyl radicals, paving way assembly FSO2 group. Based on concept, three Cu(I)-catalyzed protocols involving site-selective intra- intermolecular fluorosulfonylation inert C(sp3)–H bonds 1,2-aminofluorosulfonylation inactivated alkenes have developed, enabling preparation C(sp3)-rich aliphatic fluorides cannot be easily synthesized by known methods. These practical operationally methods result in high functional group tolerance under mild conditions modification bioactive derivatives highly valued molecules. Detailed mechanistic studies indicate unique role facilitating such rare FATs via outer-sphere pathway.

Язык: Английский

Процитировано

15

Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides DOI

Lu Lin,

Guanhua Pei,

Zhong‐Yan Cao

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(23)

Опубликована: Май 25, 2024

Abstract Sulfonyl fluorides have widespread applications in many fields, including organic synthesis, chemical biology, drug discovery and materials science. In particular, the past decade, a number of aliphatic sulfonyl been identified showing various biological activities. These appealing features brought about significant advancement developing synthetic methods to access fluorides. this review, we will discuss recent developments radical approaches for synthesis

Язык: Английский

Процитировано

11

Electroreduction strategy: a sustainable tool for the generation of aryl radicals DOI
Xiaoqing Xie,

Wei Zhou,

Ruchun Yang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4318 - 4342

Опубликована: Янв. 1, 2024

This review primarily focuses on the generation of aryl radicals via an electroreduction strategy, and systematically elaborates synthetic applications, scope, limitations substrates.

Язык: Английский

Процитировано

9

Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization DOI
Zhengyang Chen, Dan Xiong, Nengzhong Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(10), С. 2762 - 2767

Опубликована: Янв. 1, 2024

A P(NMe2)3-catalyzed [4 + 2] annulation of 2-amino-β-nitrostyrenes and β′-acetoxy allenoates followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization has been developed.

Язык: Английский

Процитировано

8

The Strategies towards Electrochemical Generation of Aryl Radicals DOI
Xiaobao Zeng

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Июль 16, 2024

The advancement in electrochemical techniques has unlocked a new path for achieving unprecedented oxidations and reductions of aryl radical precursors controlled selective manner. This approach facilitates the construction aromatic carbon-carbon carbon-heteroatom bonds. In light green merits growing importance this technique chemistry, review aims to provide an overview recent advance generation radicals organized by precursor type, with focus on substrate scope, limitation, underlying mechanism, thereby inspiring future work generation.

Язык: Английский

Процитировано

7

Accessing Benzoazepine Derivatives via Photoinduced Radical Relay Formal [5 + 2] Reaction of Amide/Alkyne Enabled by Palladium Catalysis DOI

Yu-jia Du,

Xia-xin Sheng,

Luning Tang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(13), С. 2662 - 2667

Опубликована: Март 26, 2024

A novel class of alkyne-tethered amides facilitates an unprecedented photoinduced palladium-catalyzed radical relay formal [5 + 2] reaction. This innovative strategy allows for the rapid construction diverse fused benzoazepine structures, yielding structurally and compelling compounds. With a broad substrate scope excellent functional group tolerance, methodology synthesizes biologically active Notably, resulting tricyclic benzo[b]azepines offer diversification opportunities through simple transformations. DFT calculations elucidate seven-membered ring closure mechanism involving alkenyl Pd(I) rebound alongside concerted metalation–deprotonation (CMD) process.

Язык: Английский

Процитировано

5

CoH-catalyzed asymmetric remote hydroalkylation of heterocyclic alkenes: a rapid approach to chiral five-membered S- and O-heterocycles DOI Creative Commons
Lingzi Zhao,

Feipeng Liu,

Yan Zhuang

и другие.

Chemical Science, Год журнала: 2024, Номер 15(23), С. 8888 - 8895

Опубликована: Янв. 1, 2024

A highly efficient method achieves precise construction of alkyl chiral centers at remote C3-positions in five-membered S/O-heterocycles via cobalt-catalyzed asymmetric hydroalkylation heterocyclic alkenes.

Язык: Английский

Процитировано

4

Enantioconvergent and diastereoselective synthesis of atropisomeric hydrazides bearing a cyclic quaternary stereocenter through ternary catalysis DOI Creative Commons
Xia Wang, Shaojie Wang,

Xiaolan Xin

и другие.

Chemical Science, Год журнала: 2024, Номер 15(33), С. 13240 - 13249

Опубликована: Янв. 1, 2024

The enantioselective and diastereoselective synthesis of atropisomeric hydrazides with defined vicinal central axial chirality via ternary catalysis in a one-pot process is reported.

Язык: Английский

Процитировано

4

Electrochemical Denitrative Cyclization Driven by Alternating Polarity DOI
Shu Zhu, Yichao Lin,

Guo-Cai Yuan

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 29, 2025

Alternating current electrolysis has emerged as a promising technique for addressing challenging redox reactions that are otherwise difficult or impossible direct electrolysis. Under mild and transition-metal-free reaction conditions, general electrochemical denitrative cyclization of nitroarenes was developed to access various cyclic sulfone-containing derivatives biological significance. The key success lies in the facile manipulation multiple events upon rapid alternating polarity switching enhance selectivity efficiency.

Язык: Английский

Процитировано

0

Denitrative Functionalization of Nitroarenes: Recent Progress and Future Perspectives DOI
Haiyan Li,

Zhiguo Lei,

Xun Yang

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(45)

Опубликована: Авг. 27, 2024

Abstract Nitroarenes are fundamental feedstocks in the chemical industry. Their relatively inert C−NO 2 bond allows for late‐stage modifications of molecules and exhibits complete orthogonality to reactivity C‐halogen cross‐coupling reactions. The denitrative functionalization nitroarenes holds significant appeal due it avoids use aryl halides, thereby simplifying reaction steps improving atom step economy. Recent progress direct includes palladium‐catalyzed coupling, copper‐catalyzed as well metal‐free one‐pot functionalization. In this review, we provide a concise overview these advancements, detailing features mechanisms. This summary aims highlight versatility efficiency methodologies, offering insights into their potential applications inspiring further research promising area organic synthesis.

Язык: Английский

Процитировано

3