Reactivity and mechanistic insight into the cross coupling reaction between isochromans and β-keto esters through C–H bond activation under visible light irradiation
Literature Information
Publication Date
2016-02-10
DOI
10.1039/C5QO00412H
Impact Factor
5.281
Authors
Ming Xiang, Qing-Yuan Meng, Xue-Wang Gao, Tao Lei, Bin Chen, Chen-Ho Tung, Li-Zhu Wu
View Original
Abstract
The visible light catalytic cross coupling reaction from two different C–H bonds provides an efficient protocol for C–H bond activation and C–C bond construction. The application of the oxidative photoredox strategy to couple C–H bonds next to an oxygen atom with other C–H bonds is more challenging because of the more positive oxidation potential of ethers than that of amines. Here, we take advantage of organic dye 9-mesityl-10-methylacridinium perchlorate (Acr+-Mes ClO4−) as the photosensitizer and BrCCl3 as the terminal oxidant to achieve the addition of β-keto esters to oxonium species, directly generated from isochromans, leading to the formation of alkylation products in the α-position of an oxygen atom under visible light irradiation.
Recommended Journals
Saudi Pharmaceutical Journal
Russian Journal of Applied Chemistry
Chemical Communications
Chemistry Education Research and Practice
Current Opinion in Solid State & Materials Science
Acta Materialia
Russian Journal of General Chemistry
Journal of Saudi Chemical Society
Crystallography Reports
Russian Chemical Bulletin
Related Literature
Synthesis of polyethylene and polystyrene miktoarm star copolymers using an “in–out” strategy
Bo-Geng Li
2014-05-23
Paper
DOI: 10.1039/C4PY00622D
Rapid, semi-automated convergent synthesis of low generation triazine dendrimers using microwave assisted reactions
Alan E. Enciso, Zachary M. Abid, Eric E. Simanek
2014-04-15
Paper
DOI: 10.1039/C4PY00349G
In vitro and in vivo application of hydroxypropyl-β-cyclodextrin-grafted polyethyleneimine used as a transdermal penetration enhancer
Ke Wang, Yan Yan, Guilan Zhao, Wei Xu, Kai Dong, Cuiyu You, Lu Zhang, Jianfeng Xing
2014-03-14
Paper
DOI: 10.1039/C4PY00286E
Synthesis and phase behavior of a new 2-vinylbiphenyl-based mesogen-jacketed liquid crystalline polymer with a high glass transition temperature and low threshold molecular weight
Qi-Kai Zhang, Hai-Jian Tian, Yu-Feng Zhu, Yongri Liang, Zhihao Shen, Xing-He Fan
2014-03-11
Paper
DOI: 10.1039/C3PY01755A
Trehalose-functionalized block copolymers form serum-stable micelles
Swapnil R. Tale, Ligeng Yin, Theresa M. Reineke
2014-04-29
Paper
DOI: 10.1039/C4PY00399C
Synthesis of 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, and 12-armed star-shaped poly(styrene oxide) Ru(ii) complexes by a click-to-chelate approach
Yougen Chen, Nao Xiao, Toshifumi Satoh, Toyoji Kakuchi
2014-04-15
Paper
DOI: 10.1039/C4PY00314D
Structure related transport properties and cellular uptake of hyperbranched polyglycerol sulfates with hydrophobic cores
Florian Paulus, Dirk Steinhilber, Pia Welker, Dorothea Mangoldt, Kai Licha, Harald Depner, Stephan Sigrist, Rainer Haag
2014-05-15
Paper
DOI: 10.1039/C4PY00430B
SARA ATRP or SET-LRP. End of controversy?
Dominik Konkolewicz, Yu Wang, Pawel Krys, Mingjiang Zhong, Abdirisak A. Isse, Armando Gennaro, Krzysztof Matyjaszewski
2014-05-15
Minireview
DOI: 10.1039/C4PY00149D
You might also like
Compound Q&A
What is Ethyl 3-cyclohexylpropanoate (CAS: 10094-36-7)?
Ethyl 3-cyclohexylpropanoate is a clear, colorless to light yellow liquid with a...
10094-36-7Ethyl 3-cyclohexylpr...
Compound Q&A
How should waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl)nicotinic acid (CAS: 34783-31-8) be handled?
Waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl...
34783-31-82-(Hydroxymethyl)-5-...
Compound Q&A
How should waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) be handled?
Waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) sho...
858-46-82,4,6-Tris(pentafluo...
Compound Q&A
What precautions should be taken when handling Chloroac-nle-oh (CAS: 56787-36-1)?
When handling Chloroac-nle-oh (CAS: 56787-36-1), it is essential to wear appropr...
56787-36-1Chloroac-nle-oh
Compound Q&A
What industries use Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 752244-05-6)?
Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate is primarily used in the...
752244-05-6Ethyl 6-phenylimidaz...
Compound Q&A
Are there alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis?
Alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis ...
55095-15-3alpha-(2-Bromophenyl...
Compound Q&A
How should waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) be handled?
Waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) should be managed...
139585-48-12-Chloro-5-methoxypy...
Compound Q&A
What industries use 1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9)?
1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9) is used in various ...
5044-27-91-(4-Methoxyphenyl)-...
Compound Q&A
Are there alternatives to 3-Bromo-5-(N-Boc)aminomethylisoxazole (CAS: 903131-45-3) in synthesis?
There are alternative reagents and compounds that can be used in the synthesis o...
903131-45-33-Bromo-5-(N-Boc)ami...
Compound Q&A
What is Tungsten(IV) oxide (CAS: 12036-22-5)?
Tungsten(IV) oxide, also known as tungsten dioxide, is a chemical compound with ...
12036-22-5Tungsten(IV) oxide
Source Journal
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
![3-[(4-Nitrobenzyl)oxy]-3-oxopropanoic Acid structure](https://static.chemtradehub.com/structs/773/77359-11-6-0d04.webp "3-[(4-Nitrobenzyl)oxy]-3-oxopropanoic Acid structure")
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.