Eucalyptol as a Bio-Based Solvent for Buchwald-Hartwig Reaction on O,S,N-Heterocycles
Abstract
:1. Introduction
2. Results and Discussion
2.1. From 2-Bromofluorene
2.2. From 4-Bromo-1,2-methylenedioxybenzene
2.3. From 6-Bromo-2-methylquinoline
2.4. From 7-Bromo-6-phenylthieno[2,3-b]pyrazine and 3-Bromo-2-phenylthieno[3,2-b]pyridine
2.5. Recyclability of the Solvent
3. Materials and Methods
General Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Entry | Pd (5 mol%) | Ligand (10 mol%) | Base (2 eq.) | t (h) | Yield(%) |
---|---|---|---|---|---|
1 | Pd(OAc)2 | TTBP.HBF4 | K2CO3 | 30 | 72 |
2 | Pd(OAc)2 | TTBP.HBF4 | K3PO4 | 24 | 80 |
3 | Pd(OAc)2 | TTBP.HBF4 | Cs2CO3 | 24 | 81 |
4 | Pd(OAc)2 | BINAP | K2CO3 | 30 | 60 |
5 | Pd(OAc)2 | BINAP | K3PO4 | 17 | 36 |
6 | Pd(OAc)2 | BINAP | Cs2CO3 | 17 | 87 |
7 | Pd(OAc)2 | Xantphos | K2CO3 | 40 | 57 |
8 | Pd(OAc)2 | Xantphos | K3PO4 | 17 | 72 |
9 | Pd(OAc)2 | Xantphos | Cs2CO3 | 40 | 68 |
10 | Pd(OAc)2 | PPh3 | K2CO3 | 40 | Traces |
11 | Pd(OAc)2 | PPh3 | K3PO4 | 40 | 66 |
12 | Pd(OAc)2 | PPh3 | Cs2CO3 | 40 | 32 |
13 | Pd2dba3 | TTBP.HBF4 | K3PO4 | 48 | 40 |
14 | Pd2dba3 | TTBP.HBF4 | Cs2CO3 | 48 | 38 |
15 | Pd2dba3 | BINAP | Cs2CO3 | 20 | 67 |
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Campos, J.F.; Berteina-Raboin, S. Eucalyptol as a Bio-Based Solvent for Buchwald-Hartwig Reaction on O,S,N-Heterocycles. Catalysts 2019, 9, 840. https://doi.org/10.3390/catal9100840
Campos JF, Berteina-Raboin S. Eucalyptol as a Bio-Based Solvent for Buchwald-Hartwig Reaction on O,S,N-Heterocycles. Catalysts. 2019; 9(10):840. https://doi.org/10.3390/catal9100840
Chicago/Turabian StyleCampos, Joana F., and Sabine Berteina-Raboin. 2019. "Eucalyptol as a Bio-Based Solvent for Buchwald-Hartwig Reaction on O,S,N-Heterocycles" Catalysts 9, no. 10: 840. https://doi.org/10.3390/catal9100840