B2(OH)4 and Et3N-BH3: A New Combination of Reagents for the Mild and Efficient Photoreduction of Nitro(hetero)arenes DOI

Piotr T. Błyszczyk,

Baptiste Roure

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract Anilines are a common motif in many bioactive compounds and their production through the reduction of nitroarenes has become an essential method for synthesis. We demonstrate that combination amine-borane complex hypoboric acid (tetrahydroxydiborane) under visible light irradiation can accomplish to corresponding anilines. Preliminary mechanistic studies suggest generation boryl radicals via hydrogen atom transfer (HAT) step from photoexcited nitroarene. Involvement parallel thermal pathway is demonstrated with high reaction efficiency being partially attributed both routes.

Language: 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

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2638 - 2664

Published: Jan. 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.

Language: Английский

Citations

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

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(18)

Published: March 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.

Language: Английский

Citations

4

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

Z. M. Wang

et al.

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

Published: Jan. 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.

Language: Английский

Citations

0

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

Jianqun Liu,

Hongli Liu

et al.

Journal of Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 116050 - 116050

Published: Feb. 1, 2025

Language: Английский

Citations

0

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

Qini Li,

Yi-Hui Deng

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 3, 2025

Language: Английский

Citations

0

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

et al.

Published: Jan. 1, 2025

Language: Английский

Citations

0

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

Dongcheng Zheng

et al.

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

Published: May 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.

Language: Английский

Citations

0

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

Yu‐Feng Zhang,

Emmanuelle Schulz, Mohamed Mellah

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: May 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 %.

Language: Английский

Citations

2

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

Xianglin Zhong

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 14, 2024

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

Language: Английский

Citations

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

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 9, 2024

A novel protocol for the Cu-catalyzed reductive

Language: Английский

Citations

2