Photoredox-catalyzed synthesis of sulfonated oxazolines from N-allylamides through the insertion of sulfur dioxide
Literature Information
Publication Date
2021-11-30
DOI
10.1039/D1QO01540K
Impact Factor
5.281
Authors
Zhichao Chen, Hong Zhang, Shu-Feng Zhou, Xiuling Cui
View Original
Abstract
Photoredox-catalyzed generation of sulfonated oxazolines starting from N-allylamides, DABCO·(SO2)2, and aryldiazonium salts has been developed. A range of sulfonated oxazolines were obtained in moderate to good yields. This transformation involves the sequential insertion of sulfur dioxide, intermolecular sulfonylation of alkenes and intramolecular cyclization via a radical process. This protocol features good compatibility of functional groups and mild reaction conditions. Sulfonated oxazolines could be efficiently transformed into β-amino alcohol, which is an important moiety in pharmaceuticals.
Related Literature
Facile synthesis of the daphnane and tigliane framework by semi-flow tube-based-bubbling photooxidation and diastereoselective conjugate addition
Zhengwei Ding, Zhi Liu, Guanghu Tong, Linlin Hu, Yangqing He, Yueyun Bao, Zhouhang Lei, Hailong Zhang
2020-06-09
Research Article
DOI: 10.1039/D0QO00424C
Copper-catalyzed trifluoromethylthiolation-peroxidation of alkenes and allenes
Yuanjin Chen, Yangyang Ma, Liangkui Li, Mingshuo Cui, Zhiping Li
2020-06-02
Research Article
DOI: 10.1039/D0QO00533A
Diastereoselective synthesis of 3,3-disubstituted 3-nitro-4-chromanone derivatives as potential antitumor agents
Huiqing Chen, Jia Xie, Dong Xing, Jinping Wang, Jie Tang, Zhengfang Yi, Fei Xia, Wen-Wei Qiu, Fan Yang
2019-01-07
Communication
DOI: 10.1039/C8OB02761G
Hydroaminoalkylation of sterically hindered alkenes with N,N-dimethyl anilines using a scandium catalyst
Jianhong Su, Yiqun Zhou, Xin Xu
2018-12-10
Paper
DOI: 10.1039/C8OB02657B
A metal-free aromatic cascade for the synthesis of diverse heterocycles
Steven C. Schlitzer, Dhanarajan Arunprasath, Katelyn G. Stevens, Indrajeet Sharma
2020-01-02
Research Article
DOI: 10.1039/C9QO01336A
A hydrate salt-promoted reductive coupling reaction of nitrodienes with unactivated alkenes
Mengmeng Zhang, Liming Yang, Chao Tian, Meng Zhou, Guangming Li
2019-01-31
Paper
DOI: 10.1039/C9OB00136K
Posttranscriptional spin labeling of RNA by tetrazine-based cycloaddition
Christof Domnick, Gregor Hagelueken, Frank Eggert, Olav Schiemann, Stephanie Kath-Schorr
2018-11-28
Communication
DOI: 10.1039/C8OB02597E
Recent developments in palladium-catalyzed C–S bond formation
Jianxiao Li, Shaorong Yang, Wanqing Wu, Huanfeng Jiang
2020-04-22
Review Article
DOI: 10.1039/D0QO00377H
You might also like
Compound Q&A
What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?
(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...
16326-97-9(1R,3S)-1,3-Cyclopen...
Compound Q&A
What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?
When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...
637-31-0N'-[4-(Dimethylamino...
Compound Q&A
Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?
There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...
1352318-16-15-(2,4-Difluoropheny...
Compound Q&A
What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?
1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...
382141-68-61-(3-Methoxyphenoxy)...
Compound Q&A
Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?
Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...
18660-81-6Tetrodotoxin Citrate
Compound Q&A
What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?
2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...
225641-84-92-Methyl-2-propanyl ...
Compound Q&A
How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?
Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...
16261-80-64-(2-Hydroxyhexafluo...
Compound Q&A
How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?
2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...
102507-19-72-Methyl-2-propanyl ...
Compound Q&A
What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?
Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...
20735-15-3Benzeneethanamine, α...
Compound Q&A
Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?
In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...
20691-84-33-{(E)-[4-(Dimethyla...
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
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.