Copper-Catalyzed Synthesis of Substituted Primary Arylamines from Cyclohexenone Oxime Esters DOI
Y. Kuang, Yan Yu, Min Zhou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(48), P. 8655 - 8660

Published: Nov. 29, 2023

A novel protocol has been developed for the Cu-catalyzed synthesis of primary arylamines with meta-substituents using cyclohexenone oxime esters. Mechanistic insights suggest that reaction proceeds via an intermolecular 1,5-H hydrogen atom transfer imine radical intermediate. This approach features high efficiency, a readily available catalyst system, and broad functional group tolerance.

Language: Английский

1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls DOI Creative Commons

Yuqiang Zhou,

Kui-Cheng He,

Weihao Zheng

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(20), P. 7502 - 7514

Published: Jan. 1, 2024

The exploitation of new reactive species and novel transformation modes for their synthetic applications have significantly promoted the development organic methodology, drug discovery, advanced functional materials. α-Iminyl radical cations, a class distonic ions, exhibit great potential synthesis valuable molecules. For generation, conjugate addition to α,β-unsaturated iminium ions represents concise yet highly challenging route, because

Language: Английский

Citations

5

I2/Amine Synergistic Catalysis Enables 2,2’-Bipyridine Synthesis from Oxime Esters and Enals DOI
Xing Jin, Jiahao Zhou, Hao Zeng

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A synergistic I2/secondary amine catalysis has been developed for the modular assembly of 2,2'-bipyridines, employing oxime esters and enals as readily available starting materials. This method demonstrates a good substrate scope functional group tolerance can easily afford series structurally new 2,2'-bipyridines in moderate to yields.

Language: Английский

Citations

0

Copper-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones DOI

Zi-Jun Hu,

Wei Chen,

Xinyu Lyu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4229 - 4234

Published: May 13, 2024

A copper-catalyzed [3 + 2] annulation of

Language: Английский

Citations

3

DABCO‐Promoted Selective Photochemical C−N Coupling: Access to Unsymmetrical Azahelicenes DOI
R. Yu. Balakhonov, I. S. Mekeda, Валерий З. Ширинян

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(21), P. 3690 - 3703

Published: Sept. 16, 2023

Abstract A multifaceted study on the effect of various factors efficiency photocyclization naphthofuran O‐acyl oximes was performed. It showed that without any additives or in presence electron acceptors, reaction occurs by a radical pathway and with low chemoselectivity, while DABCO promotes intramolecular cyclization to give naphthofuroquinolines (NFQs) 34–87% yields. The iminyl formed under UV irradiation due single transfer (SET) N−O bond cleavage undergoes selective homolytic aromatic substitution (HAS) formation new C−N bond. This route quinoline‐annulated scaffolds is based use both as an agent proton acceptor.

Language: Английский

Citations

9

Synthesis of multisubstituted carbazol-4-amines from tetrahydrocarbazol-4-one oximes DOI
Jiahua Wang, Dandan Gao, Aanuoluwapo O. Oyejobi

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2821 - 2828

Published: Jan. 1, 2024

A sequential synthetic method toward 1,3-disubstituted carbazol-4-amines is reported and an interesting C–S metathesis process disclosed.

Language: Английский

Citations

1

The Construction of Furocoumarins through Iron-Catalyzed Relay Annulation of Oxime Esters with 4-Hydroxycoumarins DOI
Kun Jiang,

Qing-Peng Liu,

Yuqiang Zhou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8741 - 8746

Published: Oct. 10, 2024

An iron-catalyzed relay annulation protocol was disclosed, which utilizes oxime esters and 4-hydroxycoumarins as the readily available starting materials showcases broad substrate scope good functional group tolerance. This method allows simultaneous generation of two C-C one C-O bonds rings in step, affording structurally new furocoumarins moderate to yields.

Language: Английский

Citations

1

Ortho C–H Bond Activations in an Atmospheric Microwave Plasma Ion Source DOI
Guan‐Ru Chen, Fengjian Chu, Shuheng Zhang

et al.

Journal of the American Society for Mass Spectrometry, Journal Year: 2024, Volume and Issue: 35(5), P. 951 - 959

Published: April 10, 2024

C-H bond ortho-substitution reaction has always been a significant and challenging topic in organic chemistry. We proposed synthesis method based on microwave plasma torches. High-resolution mass spectrometry was used to monitor rapid products. 2-Alkylbenzimidazole can be formed through the of phenylnitrenium ion nitriles millisecond scale. This achieve one-step formation benzimidazoles from benzene ring single-substituted compounds without addition external oxidants or catalysts. A similar activation accomplished with ketones. Meanwhile, reactor modified, resulting 2-methylbenzimidazole successfully collected, indicating device good application potential reactions such as reaction.

Language: Английский

Citations

0

Synthesis of 2H-imidazoles via Copper-Catalyzed Homo/Cross-Coupling of Oxime Acetates DOI
Min Liu, Bifu Liu, Hongyan Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(36), P. 7316 - 7320

Published: Jan. 1, 2024

A facile and practical protocol to construct 2 H -imidazoles by applying an oxime acetate block as the sole component via homo/cross-coupling catalyzed Cu( i ) was developed.

Language: Английский

Citations

0

NaOAc-Promoted [3+1+2] Annulation of O-Pivaloyl Oximes, Aldehydes, and 2-Methylbenzothiazole Salts: Synthesis of 1-Azaphenothiazines DOI
Baihui Liang,

Xiangya Cai,

Shengting Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13438 - 13449

Published: Sept. 5, 2024

This paper presents an efficient strategy for constructing 1-azaphenothiazines through the NaOAc-promoted [3+1+2] annulation of

Language: Английский

Citations

0

Copper-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with p-Hydroquinones for the Synthesis of 5-Hydroxyindoles DOI

Hui-Peng Zhang,

Wei Chen,

Zi-Jun Hu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 4, 2024

A copper-catalyzed [3 + 2] annulation of

Language: Английский

Citations

0