Site-selective C–H difunctionalization of N-alkyl activated azaarenes via the synergistic catalysis of graphene oxide and visible light

Literature Information

Publication Date 2023-09-26
DOI 10.1039/D3QO01375H
Impact Factor 5.281
Authors

De-Hao Duan, Hai-Ping He, Wei-Yi Ding, Dong-Cheng Yi, Ying-Zhen Lai, Ai-Qiong Huang, Jie Liu, Wen-Le Wu, Xiang-Jun Peng


View Original

Abstract

Strategies for site-selective C–H difunctionalization on N-alkyl activated azaarenes have attracted considerable attention as a powerful tool in heterocyclic chemistry. By employing graphene oxide (GO) as a heterogeneous cocatalyst, the visible light-induced site-selective difunctionalizations of pyridiniums/quinoliniums provided a distinct and straightforward synthetic route toward C4- and C2-selective phosphonation of the pyridinone/quinolinone/quinolone cores. Furthermore, the site-selectivity on quinoliniums could be successfully switched from C4 to C2 by changing the base and solvent. This coordination of catalysis systems drove the regioselective phosphonyl radical and phosphoryl anion addition to N-alkyl activated azaarenes, respectively, and subsequent oxidation with air as the terminal oxidant. In vitro antitumor studies showed that complex 3c participated in mitochondria-mediated pathways on the apoptosis of HeLa cells to 42.2% (21 μM). Phosphorus-based organocatalyst 4e, as one of the optical materials, offered efficient tuning of the emission and quantum yields.

Related Literature

The influence of transition metal oxides on the kinetics of Li2O2 oxidation in Li–O2 batteries: high activity of chromium oxides

Koffi P. C. Yao, Yi-Chun Lu, Chibueze V. Amanchukwu, David G. Kwabi, Marcel Risch, Jigang Zhou, Alexis Grimaud, Paula T. Hammond, Fanny Bardé

2013-11-29 Paper

DOI: 10.1039/C3CP53330A

Front cover

Cover

DOI: 10.1039/C3CP90149A

The quantum-chemical approach to calculations of thermodynamic and structural parameters of formation of fatty acid monolayers with hexagonal packing at the air/water interface

Yu. B. Vysotsky, E. A. Belyaeva, E. S. Fomina, D. Vollhardt, V. B. Fainerman, R. Miller

2013-12-19 Paper

DOI: 10.1039/C3CP54124J

A XANES study of LiVPO4F: a factor analysis approach

Yan Qin, Yang Ren, Steve M. Heald, Chengjun Sun, Dehua Zhou, Bryant J. Polzin, Steve E. Trask, Khalil Amine, Yinjin Wei, Gang Chen, Ira Bloom, Zonghai Chen

2014-01-10 Paper

DOI: 10.1039/C3CP54588A

Electron impact induced anion production in acetylene

Ewelina Szymańska, Iztok Čadež, E. Krishnakumar, Nigel J. Mason

2013-11-27 Paper

DOI: 10.1039/C3CP54459A

Experimental and theoretical study of the electronic properties of Cu-doped anatase TiO2

Javier Navas, Antonio Sánchez-Coronilla, Teresa Aguilar, Desireé M. de los Santos, Jesús Sánchez-Márquez, David Zorrilla, Concha Fernández-Lorenzo, Rodrigo Alcántara, Joaquín Martín-Calleja

2013-11-25 Paper

DOI: 10.1039/C3CP54273D

Modeling and simulation of the water gradient within a Nafion membrane

Masoumeh Ozmaian

2014-01-09 Paper

DOI: 10.1039/C3CP54015D

Adsorption studies of a phosphonic acid on ITO: film coverage, purity, and induced electronic structure changes

S. A. Paniagua, E. L. Li, S. R. Marder

2013-12-19 Paper

DOI: 10.1039/C3CP54637C

You might also like

Compound Q&A

What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?

N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...

52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A

What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?

When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...

1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A

What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?

Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...

628-39-7Diethyldiselane
Compound Q&A

What is the market or research trend for oxocopper (CAS: 12053-18-8)?

The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...

12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A

What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?

The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...

1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A

What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?

2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...

35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A

What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?

2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...

91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A

How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?

(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...

129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A

What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?

3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...

4857-42-53-Methyl-1,2-oxazole...
Compound Q&A

How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?

Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...

1281816-04-3Lys-SMCC-DM1

Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.