Palladium/norbornene/copper-catalysed intermolecular thio-esterification from ketones: modular access towards tetrasubstituted vinyl sulfides
Literature Information
Publication Date
2023-11-07
DOI
10.1039/D3QO01484C
Impact Factor
5.281
Authors
Guopeng Du, Yu Zhao, Pingliang Zhu, Shaowen Ling, Baolong Xu, Hui Liu, Xinjin Li, Feng-Gang Sun
View Original
Abstract
Herein, we disclosed a strategy to access diverse tetrasubstituted vinyl sulfides from cyclic ketones via palladium/norbornene/copper catalysed dual functionalization of the corresponding enol triflates, allowing simultaneous installation of thio and alkoxycarbonyl groups at vicinal positions of 1,2-disubstiuted alkene in a regioselective fashion. A copper salt was proven to enhance the reactivity of the electrophile to achieve the desired selectivity without using commonly used C2 amide-substituted norbornene. Readily available thiocarbonates are suitable bifunctional electrophiles; various functional groups could be tolerated. The protocol is scalable and permits orthogonal coupling in the presence of other functionalization handles.
Recommended Journals
Related Literature
A new approach to determine vapour pressures and hygroscopicities of aqueous aerosols containing semi-volatile organic compounds
D. J. Stewart, T. C. Preston, J. S. Walker, Y.-H. Zhang, J. P. Reid
2014-01-02
Paper
DOI: 10.1039/C3CP54948H
Reactions of HOCO radicals through hydrogen-atom hopping utilizing clathrate hydrates as an observational matrix
Motoi Oshima, Atsushi Tani, Takeshi Sugahara, Katsuhisa Kitano, Kazunari Ohgaki
2013-12-18
Paper
DOI: 10.1039/C3CP54680B
Plasmon-enhanced water splitting on TiO2-passivated GaP photocatalysts
Jing Qiu, Guangtong Zeng, Prathamesh Pavaskar, Zhen Li
2013-12-20
Paper
DOI: 10.1039/C3CP54674H
Determination of volatility of ionic liquids at the nanoscale by means of ultra-fast scanning calorimetry
Mathias Ahrenberg, Marcel Brinckmann, Jürn W. P. Schmelzer, Martin Beck, Christin Schmidt
2013-11-15
Paper
DOI: 10.1039/C3CP54325K
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
Tuning photocatalytic performance of the near-infrared-driven photocatalyst Cu2(OH)PO4 based on effective mass and dipole moment
Zhujie Li, Ying Dai, Xiangchao Ma, Yingtao Zhu, Baibiao Huang
2013-11-11
Paper
DOI: 10.1039/C3CP53381F
Electro-reduction of nitrogen on molybdenum nitride: structure, energetics, and vibrational spectra from DFT
Fernando H. Garzon, Neil J. Henson
2013-12-13
Paper
DOI: 10.1039/C3CP54559H
Competitive pi interactions and hydrogen bonding within imidazolium ionic liquids
Richard P. Matthews, Tom Welton, Patricia A. Hunt
2014-01-09
Paper
DOI: 10.1039/C3CP54672A
CO2-induced micelle to vesicle transition in zwitterionic–anionic surfactant systems
Wei Li, Yanjuan Yang, Tian Luo, Jianling Zhang, Buxing Han
2013-12-18
Paper
DOI: 10.1039/C3CP54537G
Kinetically controlled seed-mediated growth of narrow dispersed silver nanoparticles up to 120 nm: secondary nucleation, size focusing, and Ostwald ripening
Ruilong Zong, Shikao Shi, Yongfa Zhu
2014-01-06
Paper
DOI: 10.1039/C3CP54846E
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
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
![1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure](https://static.chemtradehub.com/structs/122/1226872-27-0-e037.webp "1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure")
1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone
CAS Number:
1226872-27-0
Molecular Formula:
C25H26N6O4
2-Methyl-2-propanyl 2-carbamimidoyl-1-piperidinecarboxylate
CAS Number:
1258640-98-0
Molecular Formula:
C11H21N3O2
2-(4,4-Difluorobutyl)-1H-isoindole-1,3(2H)-dione
CAS Number:
1265341-14-7
Molecular Formula:
C12H11F2NO2
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.