Efficient Amide Formation from Non‐Activated Cyclopropyl Ester via Acyl Fluoride Generation Using Hypervalent Iodine(III) Reagent and Selectfluor DOI Open Access
Eunsol Choi,

Hee‐Chan Jeong,

Ye‐Lin Han

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(9)

Published: July 27, 2023

Abstract A novel and unique activation method for esters possessing a non‐activated cyclopropyl moiety as potential activating group is developed acyl fluoride generation using hypervalent iodine(III) reagent Selectfluor. The resulting fluoride, which versatile synthetic intermediate, was smoothly transformed into the various carbonyl compounds, in particular, amides. This protocol can be applied to chemoselective of diester compounds.

Language: Английский

Anaerobic Hydroxylation of C(sp3)–H Bonds Enabled by the Synergistic Nature of Photoexcited Nitroarenes DOI Creative Commons
Joshua Paolillo,

Alana Duke,

Emma Gogarnoiu

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(5), P. 2794 - 2799

Published: Jan. 25, 2023

A photoexcited-nitroarene-mediated anaerobic C-H hydroxylation of aliphatic systems is reported. The success this reaction due to the bifunctional nature photoexcited nitroarene, which serves as bond activator and oxygen atom source. Compared previous methods, approach cost- atom-economical commercial availability sole mediator reaction. Because conditions transformation, a noteworthy expansion in substrate scope can be obtained compared prior reports. Mechanistic studies support that nitroarenes engage successive hydrogen transfer radical recombination events with hydrocarbons, leading N-arylhydroxylamine ether intermediates. Spontaneous fragmentation these intermediates leads key products.

Language: Английский

Citations

56

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

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

Selective N-α-C–H alkylation of cyclic tertiary amides via visible-light-mediated 1,5-hydrogen atom transfer DOI
Junlei Wang,

Qinglin Xie,

Guocheng Gao

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(17), P. 4394 - 4399

Published: Jan. 1, 2023

Herein, we report an effective C–H bond activation-alkylation strategy for 2-iodobenzoyl protected cyclic amines at the N -α-position through a visible-light mediated 1,5-hydrogen atom transfer (HAT) process.

Language: Английский

Citations

19

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

16

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

15

Advances and perspectives on photochemical/electrochemical synthesis of nitrogen, sulfur, and phosphorus heteroatom containing compounds from biomass-based feedstocks DOI

Hanjing Tian,

Anping Wang, Pan Hu

et al.

Industrial Crops and Products, Journal Year: 2024, Volume and Issue: 222, P. 119738 - 119738

Published: Sept. 27, 2024

Language: Английский

Citations

6

Shining light on nitro group: distinct reactivity and selectivity DOI
Ranjan Jana, Kangkan Pradhan

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(67), P. 8806 - 8823

Published: Jan. 1, 2024

Distinct reactivity and chemoselectives of photoexcited nitroarenes under visible light irradiation such as reductive C–N coupling, anaerobic oxidation, annulation, scaffold diversification via nitrene insertion, etc. , are highlighted.

Language: Английский

Citations

5

Visible-light induced FeCl3-catalyzed reductive transamidation of N-acyl benzotriazoles with nitro compounds DOI

Riqian Zhu,

Yang Li,

Yue Shen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2095 - 2101

Published: Jan. 1, 2024

A mild and efficient visible-light promoted FeCl 3 -catalyzed reductive transamidation of N -acyl benzotriazoles with nitro compounds by PhSiH was developed.

Language: Английский

Citations

4

Ni(cod)(duroquinone)-Catalyzed C–N Cross-Coupling for the Synthesis of N,N-Diarylsulfonamides DOI
Tian You, Junqi Li

Organic Letters, Journal Year: 2022, Volume and Issue: 24(36), P. 6642 - 6646

Published: Sept. 6, 2022

We report a C–N cross-coupling reaction of weakly nucleophilic N-arylsulfonamides and aryl bromides to access N,N-diarylsulfonamides using Ni(cod)(DQ) as catalyst without additional ligands. The process is compatible with electron-deficient electron-rich heteroaryl (34 examples, 21–98%) can be applied the derivatization an N-arylsulfonamide pharmaceutical compound.

Language: Английский

Citations

15