The application of nitroarenes in catalyst‐free photo‐driven reactions DOI Open Access

Kunpeng Teng,

Qian Liu, Jie Lv

et al.

ChemPhotoChem, Journal Year: 2023, Volume and Issue: 8(4)

Published: Nov. 27, 2023

Abstract Nitroarenes are usually excited to form photoexcited species in light‐induced reactions due their unique properties, leading the development of numerous related catalyst‐free photo‐induced encompassing diverse reaction types and key intermediates. This review aims summarize progress involving nitroarenes offers a brief overview future directions this field.

Language: Английский

Merging Photoinduced Iron-Catalyzed Decarboxylation with Copper Catalysis for C–N and C–C Couplings DOI

Ni Xiong,

Yang Li, Rong Zeng

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(3), P. 1678 - 1685

Published: Jan. 13, 2023

We report a photoinduced iron/copper dual-catalytic strategy for the radical decarboxylation functionalization of aliphatic carboxylic acids. The ligand-to-iron charge transfer process under light was initially occurred to generate an unstabilized alkyl radical, and copper catalyst delivered enabled subsequent coupling reactions form C–N or C–C bonds. By merging iron-catalyzed with catalysis, this system allows smooth conversion wide range acids amination, decarboxylative dehydrogenation, alkylation efficiently. A variety complex drug natural molecules is applicable, suggesting that would facilitate rapid compound library synthesis benefit discovery pharmaceutical agents.

Language: Английский

Citations

66
Recent advances in FeCl3-photocatalyzed organic reactions via hydrogen-atom transfer DOI
Xiaoya Yuan, Congcong Wang, Bing Yu

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(9), P. 109517 - 109517

Published: Jan. 21, 2024

Language: Английский

Citations

33
Decarboxylative sulfoximination of benzoic acids enabled by photoinduced ligand-to-copper charge transfer DOI Creative Commons
Peng Xu, Wanqi Su, Tobias Ritter

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(45), P. 13611 - 13616

Published: Jan. 1, 2022

Sulfoximines are synthetically important scaffolds and serve roles in drug discovery. Currently, there is no solution to decarboxylative sulfoximination of benzoic acids; although thoroughly investigated, limited substrate scope harsh reaction conditions still hold back traditional thermal aromatic functionalization. Herein, we realize the first acids via photo-induced ligand copper charge transfer (copper-LMCT)-enabled carbometalation. The transformation proceeds under mild conditions, has a broad scope, can be applied late-stage functionalization complex small molecules.

Language: Английский

Citations

43
Decarboxylative Sulfonylation of Carboxylic Acids under Mild Photomediated Iron Catalysis DOI

Yuanqi Dong,

Ni Xiong,

Zhouting Rong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2381 - 2386

Published: March 15, 2024

Organic sulfones are an important class of chemical compounds widely used in many research fields. The direct decarboxylative sulfonylation carboxylic acids is attractive but challenging, particularly when iron as a metal catalyst. Herein, we describe photoinduced iron-catalytic method for the synthesis directly using via radical-based decarboxylation. This protocol mild, highly efficient, and easy-to-operate. A broad scope carbon electrophiles could be well tolerated. mechanism involving iron-catalyzed decarboxylation, radical transfer, single-electron reduction, nucleophilic attack proposed.

Language: Английский

Citations

14
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

11
Visible-light-induced dehydrogenative amidation of aldehydes enabled by iron salts DOI Open Access
Han Gao, Lin Guo,

Yining Zhu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(19), P. 2771 - 2774

Published: Jan. 1, 2023

A direct dehydrogenative amidation reaction of aldehydes and amines under a visible light mediated ligand-to-metal charge transfer (LMCT) process was described. In this protocol, aldehyde substrates were activated by photoinduced hydrogen atom abstraction (HAA), generating acyl chloride intermediates followed nucleophilic addition amines. The synthetic method furnishes good functional group tolerance broad substrate scope toward both aliphatic aromatic components.

Language: Английский

Citations

22
Iron-Mediated Reductive Amidation of Triazine Esters with Nitroarenes DOI
Qing‐Dong Wang,

Xiang Liu,

Ya-Wen Zheng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 416 - 420

Published: Dec. 31, 2023

A reductive amidation of triazine esters with nitroarenes by using cheap iron as a reducing metal in the presence TMSCl DMF was developed. The reactions proceeded efficiently under transition metal-free conditions to give corresponding amides moderate good yields functional group compatibility. Preliminary mechanistic investigations indicated that nitrosobenzene, N-phenyl hydroxylamine, azoxybenzene, azobenzene, aniline, and N-arylformamide possibly served intermediates reaction.

Language: Английский

Citations

17
Photoinduced C−O Bond Formation through C−C Bond Cleavage of Alcohols by Suppressing Alcohol Oxidation DOI
Qiang Wu, Peng Hu

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(7), P. 1595 - 1605

Published: Feb. 3, 2024

Abstract Herein, we present a photoinduced deconstructive alkoxyamination of alkyl alcohols catalyzed by iron salts. This transformation involves the initiation alkoxy radicals through chlorine radical‐induced radical formation, followed β ‐scission and trapping resulting carbon with 2,2,6,6‐tetramethylpiperidin‐1‐yl (TEMPO). reaction exhibits broad substrate scope (40 examples), including primary secondary that are prone to oxidation combination TEMPO iron. Mechanistic investigations have revealed enhanced coordination chloride ion center inhibits OH process, thereby enabling tolerance alcohols.

Language: Английский

Citations

6
Nickel/Photoredox-Catalyzed Direct Amidation of Aldehydes with Nitroarenes via Fully Catalytic Process DOI

Ji‐Wei Sang,

Qiuhao Li,

Chi Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(24), P. 4592 - 4597

Published: June 12, 2023

A fully catalytic nickel-photoredox process for the direct amidation of aldehydes with nitroarenes was developed. In this system, and were catalytically activated by photocatalytic cycle without addition an additional reductant or oxidants, which facilitated Ni-mediated cross-coupling C-N bond under mild conditions. preliminary mechanistic study indicates a reaction pathway in nitrobenzene is directly reduced to aniline as nitrogen source.

Language: Английский

Citations

14
Visible-light-induced iron-catalyzed synthesis of N-aryl amides from nitroarenes and chloroalkanes DOI

Qun-Liang Zhang,

Wenxin Liu, Yirong Zhou

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(14), P. 5735 - 5740

Published: Jan. 1, 2023

An unprecedented straightforward reductive amidation of chloroalkanes with nitroarenes was readily accomplished by merging iron catalysis visible-light photoredox catalysis.

Language: Английский

Citations

14