A Palladium-Catalyzed 4CzIPN-Mediated Decarboxylative Acylation Reaction of O-Methyl Ketoximes with α-Keto Acids under Visible Light
Abstract
:1. Introduction
2. Results and Discussion
2.1. Optimization of the Reaction Conditions
2.2. Scope of Benzoylformic Acid
2.3. Scope of Acetophenone Oxime Ether
2.4. Gram-Scale Reaction and Further Transformation
2.5. Preliminary Mechanistic Study
3. Materials and Methods
3.1. General Information
3.2. Procedure for Preparation of 2b–2l
3.3. Preparation of O-Methyl Ketoximes 1a–1w
3.4. General Procedures for Ortho-Benzoylation of Acetophenone Oxime Ether
3.5. Gram-Scale Reaction
3.6. Further Transformation
3.7. Radical Capture Experiment
3.8. Experimental Procedure of Kinetic Isotope Effect
3.9. Determination of Superoxide Radical Anion
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Entry | [Pd] | [Photocatalyst] | [Solvent] | Yield (%) |
1 | Pd(OAc)2 | Eosin Y | PhCl | 55 |
2 | Pd(TFA)2 | Eosin Y | PhCl | 46 |
3 | PdCl2 | Eosin Y | PhCl | <5 |
4 | Pd(OAc)2 | fac-Ir(ppy)3 | PhCl | 20 |
5 | Pd(OAc)2 | Rose Bengal | PhCl | 45 |
6 | Pd(OAc)2 | 4CzIPN | PhCl | 70 |
7 | Pd(OAc)2 | 4CzIPN | CH3CN | <5 |
8 | Pd(OAc)2 | 4CzIPN | DCE | 44 |
9 | Pd(OAc)2 | 4CzIPN | AcOH | 77 |
10 a | Pd(OAc)2 | 4CzIPN | AcOH | 85 |
11 a | - | 4CzIPN | AcOH | 0 |
12 a | Pd(OAc)2 | - | AcOH | 30 |
13 a,b | Pd(OAc)2 | 4CzIPN | AcOH | 0 |
14 a,c | Pd(OAc)2 | 4CzIPN | AcOH | 10 |
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Wang, C.; Yang, S.; Huang, Z.; Zhao, Y. A Palladium-Catalyzed 4CzIPN-Mediated Decarboxylative Acylation Reaction of O-Methyl Ketoximes with α-Keto Acids under Visible Light. Molecules 2022, 27, 1980. https://doi.org/10.3390/molecules27061980
Wang C, Yang S, Huang Z, Zhao Y. A Palladium-Catalyzed 4CzIPN-Mediated Decarboxylative Acylation Reaction of O-Methyl Ketoximes with α-Keto Acids under Visible Light. Molecules. 2022; 27(6):1980. https://doi.org/10.3390/molecules27061980
Chicago/Turabian StyleWang, Cheng, Shan Yang, Zhibin Huang, and Yingsheng Zhao. 2022. "A Palladium-Catalyzed 4CzIPN-Mediated Decarboxylative Acylation Reaction of O-Methyl Ketoximes with α-Keto Acids under Visible Light" Molecules 27, no. 6: 1980. https://doi.org/10.3390/molecules27061980