B2(OH)4-Mediated Reductive Ring-Opening of N-Tosyl Aziridines by Nitroarenes: A Green and Regioselective Access to Vicinal Diamines DOI

Mengni Pan,

Yue Shen,

Yang Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8656 - 8667

Опубликована: Июнь 4, 2024

The nucleophilic ring-opening of aziridine derivatives provides an important synthetic tool for the preparation various β-functionalized amines. Amines as nucleophiles are employed to prepare synthetically useful 1,2-diamines in presence catalysts or activators. Herein, B2(OH)4-mediated reductive transformation N-tosyl aziridines by nitroarenes was developed. This aqueous protocol cheap and readily available amino sources proceeds under external catalyst-free conditions. Control experiments DFT calculations pointed situ reduction aryl amines via N-aryl boramidic acid (E) SN1-type N-tosylaziridines resultant with high regioselectivity.

Язык: Английский

Recent progress in the synthesis of N-substituted arylamines by reductive cross-coupling of nitroarenes DOI

Jing‐Hao Qin,

Wang Yao,

Jun-Yao Ouyang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2638 - 2664

Опубликована: Янв. 1, 2024

This review describes the recent advances in different reaction types and catalytic systems for construction of C–NAr S–NAr bonds by nitroaromatic reductive cross-coupling.

Язык: Английский

Процитировано

12

Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols DOI Creative Commons
Sara Gómez‐Gil, Nuria Cases, Raquel Hernández‐Ruiz

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(18)

Опубликована: Март 16, 2024

Abstract We report the efficient, sustainable one‐pot synthesis of a wide variety N ‐polyheterocycles, such as imidazo‐quinolines and quinoxalines, furoquinolines, from easily available nitroaromatics glycols via molybdenum catalytic domino reduction‐imine formation‐intramolecular cyclization‐oxidation sequence. It is worth highlighting that recycling incorporation waste carbonyl byproduct, generated in reduction step, into final compound realized. In addition, overall efficiency atom economy process are further improved owing to participation one reaction intermediate reductant allows lowering amount external reducing agent employed.

Язык: Английский

Процитировано

4

Cathodic Deoxygenative Alkylation of Nitro(hetero)arenes with Organic Halides DOI
Ziliang Wang, Jianfeng Zhou,

Z. M. Wang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 28, 2025

We have realized a cathodic deoxygenative alkylation between nitro(hetero)arenes and organic halides, employing bis(pinacolato)diboron (B2pin2) LiCl as additives to trap stabilize the generated alkyl radicals carbanions, thereby facilitating efficient N-O cleavage selective C-N bond formation. The protocol offers an economical method for synthesis of multiple aromatic(hetero) amines, without need reactive reductants exclusion air moisture. Notably, is distinguished by scalability, broad functional group compatibility, safe mild conditions, demonstrating practicality in late-stage modification various bioactive compounds.

Язык: Английский

Процитировано

0

Nickel-catalyzed C N bond formation of diarylamine between nitroarenes and aryl Grignard reagents DOI
Wangjun Guo,

Jianqun Liu,

Hongli Liu

и другие.

Journal of Catalysis, Год журнала: 2025, Номер unknown, С. 116050 - 116050

Опубликована: Фев. 1, 2025

Язык: Английский

Процитировано

0

Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents DOI Creative Commons
Qianqian Chang,

Qini Li,

Yi-Hui Deng

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Апрель 3, 2025

Язык: Английский

Процитировано

0

Nickel-Catalyzed Amination of Aryl Halides: An Exogenous Ligand-Free Approach to Primary Arylamines Using Tmsn3 DOI
Jiawei Huang, Xiaoman Li, Zhigang Lei

и другие.

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

Denitrative Iodination of Nitroarenes via Light-Promoted Reduction DOI
Ye Wang, Wenyan Zhao,

Dongcheng Zheng

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 12, 2025

Aryl iodides are essential synthons in organic synthesis, whose conventional preparations often suffer from poor selectivity or necessitate multistep procedures. Herein, we present a light-driven denitrative iodination as one-step approach that directly converts nitroarenes to iodoarenes under mild and transition-metal-free conditions. This streamlined method operates the absence of strong Brønsted acids, ensuring broad functional group tolerance, including esters, cyano groups, halides, heterocycles, while also offering operational simplicity scalability.

Язык: Английский

Процитировано

0

Electrocatalytic, Sm‐Promoted Synthesis of Aminoarenes from Nitroaromatic Derivatives in MeOH DOI Creative Commons

Yu‐Feng Zhang,

Emmanuelle Schulz, Mohamed Mellah

и другие.

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Май 3, 2024

Abstract A new mild and chemoselective method for the preparation of various aminoarenes is described, based on electrochemical catalytic reduction nitroaryl derivatives promoted by samarium salts in methanol. The reactions are carried out air, an undivided cell, at room temperature tolerate a wide range functional groups, including some reducible ones, without leading to by‐products. This procedure also effective complete challenging substrates, namely those capable coordinating metals, traditionally need drastic conditions terms pressure, reaction time or temperature. 47 examples one nitroalkane, all lead targeted reduced product yields that almost always over 90 %.

Язык: Английский

Процитировано

2

Visible Light-Mediated [1+2+2] Cycloaddition Reaction of Nitroarenes and Alkenes DOI
Mengxin Li, Molai Zhao,

Xianglin Zhong

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 14, 2024

We report a visible light-mediated [1 + 2 2] cycloaddition reaction between nitroarenes and alkenes, conducted under mild conditions, to synthesize isoxazolidines.

Язык: Английский

Процитировано

2

Copper-Catalyzed One-Pot Protocol for Reductive N-Arylation of Nitroarenes with (Hetero)aryl Chlorides in Water DOI

Peng Hong,

Li‐Fang Wang, Xinhai Zhu

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 9, 2024

A novel protocol for the Cu-catalyzed reductive

Язык: Английский

Процитировано

2