Eco-Friendly Functionalization of Ynals with Thiols under Mild Conditions
Abstract
:1. Introduction
2. Results and Discussion
2.1. Design and Optimization of the Reaction System
2.2. Scope of the Reaction
2.3. The Preparative Scale for the Synthesis of Product P1
3. Materials and Methods
3.1. General Methods and Chemicals
3.2. General Procedure for Catalytic Tests
3.2.1. Mono- and Multifunctionalization of Aldehydes with (Di)thiols
3.2.2. Bis-Functionalization of Aldehydes with Two Various Thiols
3.3. General Procedure for the Synthesis of Products P1–P32 and P36
3.4. General Procedure for the Synthesis of Products P33–P35
3.5. Synthesis of Product P1 on a Preparative Scale
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry | Solvent | Temp. [°C] | NHC-1 [mol%] | Time [e] [h] | Conv. of 1a [%] | P1:P1’ [f] [%] |
---|---|---|---|---|---|---|
1 | DCE | RT | 5 | 48 | 3 | - |
2 | DCM | RT | 5 | 48 | 4 | - |
3 | n-hexane | RT | 5 | 24 | 2 | - |
4 | MTBE | RT | 5 | 24 | 98 | 65:35 |
5 | Toluene | RT | 5 | 48 | 3 | - |
6 | Toluene | 40 | 5 | 48 | 65 | 50:50 |
7 | Toluene | 60 | 5 | 48 | 95 | 40:60 |
8 | Acetone | 60 | 5 | 4 | 100 | 90:10 |
9 | Acetone | 40 | 5 | 5 | 100 | 96:4 |
10 | Acetone | RT | 5 | 6 | 100 | 100:0 |
11 | Acetone | RT | 2.5 | 24 | 91 | 100:0 |
12 [a] | Acetone | RT | 5 | 48 | 15 | 90:10 |
13 [b] | Acetone | RT | - | 48 | 0 | - |
14 [c] | Acetone | RT | 5 | 48 | 0 | - |
15 [d] | Acetone | RT | 5 | 6 | 95 | 100:0 |
16 | - | RT | 5 | 5 | 80 | 60:40 |
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Hanek, K.; Żak, P. Eco-Friendly Functionalization of Ynals with Thiols under Mild Conditions. Int. J. Mol. Sci. 2024, 25, 9201. https://doi.org/10.3390/ijms25179201
Hanek K, Żak P. Eco-Friendly Functionalization of Ynals with Thiols under Mild Conditions. International Journal of Molecular Sciences. 2024; 25(17):9201. https://doi.org/10.3390/ijms25179201
Chicago/Turabian StyleHanek, Kamil, and Patrycja Żak. 2024. "Eco-Friendly Functionalization of Ynals with Thiols under Mild Conditions" International Journal of Molecular Sciences 25, no. 17: 9201. https://doi.org/10.3390/ijms25179201