Synthesis of 3-trifluoromethylated 1,3-butadienes via a Pd(0)-catalyzed fluorinated Heck reaction
Literature Information
Publication Date
2020-03-25
DOI
10.1039/D0RE00093K
Impact Factor
4.239
Authors
Yang Li, Meng Hao, Ming Xia, Ning Sun, Cai-Lin Zhang, Wen-Qing Zhu
View Original
Abstract
1,3-Butadienes play a key role in modern synthetic chemistry and biochemistry because they are well-known precursors for the synthesis of retinoids. A new and efficient synthesis of 3-trifluoromethylated 1,3-butadienes via a Pd(0)-catalyzed fluorinated Heck reaction is described. Without an additive, the reaction of 2-bromo-3,3,3-trifluoropropene, an abundant and ozone friendly CF3 building block, with acrylamides afforded 3-trifluoromethylated 1,3-butadienes in good to excellent yields with high regioselectivity and s-trans/s-cis ratios under mild conditions. Inspired by the concept of space–time yield for continuous reactions, the average space–time yield calculated shows that all the reactions far exceed 1 g gcat−1 h−1, which is high enough for further scale-up, suggesting that small amounts of catalyst and a very small reactor are required.
Related Literature
Azaphosphinines and their derivatives
J. Nolan McNeill, Jeremy P. Bard, Darren W. Johnson, Michael M. Haley
2023-11-24
Review Article
DOI: 10.1039/D3CS00737E
Bio-based hyperbranched epoxy resins: synthesis and recycling
Jiang Li, Dan Li, Yunke Ma, Shucun Zhou, Yu Wang, Daohong Zhang
2023-12-18
Review Article
DOI: 10.1039/D3CS00713H
Photoswitchable and long-lived seven-membered cyclic singlet diradicals for the bioorthogonal photoclick reaction
Fuqiang Hu, Cefei Zhang, Zhihao Liu, Xinyu Xie, Xiaohu Zhao, Yanju Luo, Jielin Fu, Baolin Li, Changwei Hu, Zhishan Su, Zhipeng Yu
2023-11-02
Edge Article
DOI: 10.1039/D3SC03675H
Stimuli-responsive synthetic helical polymers
María Lago-Silva, Manuel Fernández-Míguez, Rafael Rodríguez, Emilio Quiñoá, Félix Freire
2023-12-18
Review Article
DOI: 10.1039/D3CS00952A
Revolutionizing the structural design and determination of covalent–organic frameworks: principles, methods, and techniques
Yikuan Liu, Xiaona Liu, An Su, Chengtao Gong, Shenwei Chen, Liwei Xia, Chengwei Zhang, Xiaohuan Tao, Yue Li, Yonghe Li, Tulai Sun, Mengru Bu, Wei Shao, Jia Zhao, Xiaonian Li, Yongwu Peng, Yihan Zhu
2023-12-15
Review Article
DOI: 10.1039/D3CS00287J
Stepwise deprotonation of truxene: structures, metal complexation, and charge-dependent optical properties
Yumeng Guo, Herdya S. Torchon, Yikun Zhu, Zheng Wei, Zhenyi Zhang, Haixiang Han, Marina A. Petrukhina, Zheng Zhou
2023-10-31
Edge Article
DOI: 10.1039/D3SC04885C
Multiconfigurational photodynamics simulations reveal the mechanism of photodecarbonylations of cyclopropenones in explicit aqueous environments
Daniel M. Adrion, Waruni V. Karunaratne, Steven A. Lopez
2023-11-10
Edge Article
DOI: 10.1039/D3SC03805J
Designing drugs and chemical probes with the dualsteric approach
Jixiao He, Chengwei Wu, Mingyang Zhang
2023-11-22
Review Article
DOI: 10.1039/D3CS00650F
Mechanisms and models for water transport in reverse osmosis membranes: history, critical assessment, and recent developments
Hanqing Fan, Xinglin Lu, Menachem Elimelech
2023-10-27
Tutorial Review
DOI: 10.1039/D3CS00395G
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
Reaction Chemistry & Engineering
CiteScore:
0
Self-citation Rate:
8.8%
Articles per Year:
284
Reaction Chemistry & Engineering is an interdisciplinary journal reporting cutting-edge research focused on enhancing the understanding and efficiency of reactions. Reaction engineering leverages the interface where fundamental molecular chemistry meets chemical engineering and technology. Challenges in chemistry can be overcome by the application of new technologies, while engineers may find improved solutions for process development from the latest developments in reaction chemistry. Reaction Chemistry & Engineering is a unique forum for researchers whose interests span the broad areas of chemical engineering and chemical sciences to come together in solving problems of importance to wider society. All papers should be written to be approachable by readers across the engineering and chemical sciences. Papers that consider multiple scales, from the laboratory up to and including plant scale, are particularly encouraged.
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.