Catalytic Vilsmeier–Haack Reactions for C1-Deuterated Formylation of Indoles DOI
Jing Xue, Yushan Zhang,

Zhen Huan

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(22), P. 15539 - 15546

Published: Nov. 9, 2022

The Vilsmeier-Haack reaction is a powerful tool to introduce formyl groups into electron-rich arenes, but its wide application significantly restricted by stoichiometric employment of caustic POCl3. Herein, we reported catalytic version the enabled P(III)/P(V)═O cycle. This provides facile and efficient route for direct construction C1-deuterated indol-3-carboxaldehyde under mild conditions with DMF-d7 as deuterium source. products feature remarkably higher deuteration level (>99%) than previously ones are not contaminated likely unselective at other sites. present transformation can also be used transfer carbonyl groups. Further downstream derivatizations these deuterated manifested their potential applications in synthesis bioactive molecules. Mechanistic insight was disclosed from studies kinetics intermediates.

Language: Английский

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

3
Copper-promoted cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines using a peroxide-driven radical reductive strategy DOI
Huimin Jiang,

Jing‐Hao Qin,

Qing Sun

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(15), P. 4070 - 4077

Published: Jan. 1, 2022

Direct radical-mediated reductive coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines to build the C(sp 3 )–N bond using as internal reducing agents and alkyl sources is presented.

Language: Английский

Citations

13
Cobalt- or rhodium-catalyzed synthesis of 1,2-dihydrophosphete oxides via C–H activation and formal phosphoryl migration DOI Creative Commons
Shengbo Xu,

Ruijie Mi,

Guangfan Zheng

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 6012 - 6021

Published: Jan. 1, 2024

A highly stereo- and chemoselective intermolecular coupling of diverse heterocycles with dialkynylphosphine oxides has been realized

Language: Английский

Citations

2
Advances in Organophosphorus Redox Catalysis DOI Open Access
Wei Cai, You Huang

Chinese Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 41(10), P. 3903 - 3903

Published: Jan. 1, 2021

Organophosphorus reagents play very important role in organic synthesis.The development of Wittig reaction, Staudinger Appel reaction and Mitsunobu mediated by phosphine compounds is great significance scientific research industrial production.In recent decades, the on design P(III)/P(V) redox catalysis catalysts to realize catalytic mode these reactions, avoiding production stoichiometric R3P＝O has developed rapidly.This review introduces progress process each turn.The future direction this field about reactions involving prospected.

Language: Английский

Citations

15
Catalytic Vilsmeier–Haack Reactions for C1-Deuterated Formylation of Indoles DOI
Jing Xue, Yushan Zhang,

Zhen Huan

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(22), P. 15539 - 15546

Published: Nov. 9, 2022

The Vilsmeier-Haack reaction is a powerful tool to introduce formyl groups into electron-rich arenes, but its wide application significantly restricted by stoichiometric employment of caustic POCl3. Herein, we reported catalytic version the enabled P(III)/P(V)═O cycle. This provides facile and efficient route for direct construction C1-deuterated indol-3-carboxaldehyde under mild conditions with DMF-d7 as deuterium source. products feature remarkably higher deuteration level (>99%) than previously ones are not contaminated likely unselective at other sites. present transformation can also be used transfer carbonyl groups. Further downstream derivatizations these deuterated manifested their potential applications in synthesis bioactive molecules. Mechanistic insight was disclosed from studies kinetics intermediates.

Language: Английский

Citations

11