Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes
Abstract
:1. Introduction
2. Dihalobenzenes
2.1. Phenol Derivatives
2.2. Aniline Derivatives
2.3. Benzoic Acid Derivatives
Entry | Substrate | Ligand | Yield (%) | |
---|---|---|---|---|
A | B | |||
1 | 18 | Ph-DHTP | 90 | 0 |
2 | DPPF | 9 | 15 | |
3 | 19 | Ph-HTP | 63 | 0 |
4 | DPPF | 15 | 32 | |
5 | 20 | Ph-DHTP | 70 | 0 |
6 | DPPF | 29 | 21 | |
7 | 21 | Ph-DHTP | 81 | 0 |
8 | DPPF | 0 | 37 |
3. Dihaloheteroarenes
3.1. Pyrone Derivatives
Entry | CuI (equiv) | Conditions | Yield (%) | |
---|---|---|---|---|
28 | 29 | |||
1 | 0 | toluene, 100 °C, 0.5 h | 81 | trace |
2 | 0.1 | toluene, 100 °C, 0.5 h | 94 | trace |
3 | 1.0 | toluene, 100 °C, 2 h | 71 | 6 |
4 | 0 | DMF, 50 °C, 4 days | 41 | 2 |
5 | 0.1 | DMF, 50 °C, 5 h | 34 | 20 |
6 | 0.5 | DMF, 50 °C, 2.5 h | trace | 64 |
7 | 1.0 | DMF, 50 °C, 2 h | trace | 75 |
3.2. Pyridine Derivatives
Entry | R | Catalyst (mol %) | Conditions | 32:33 |
---|---|---|---|---|
1 | OMe | Pd(PPh3)4 (5) | THF, reflux, 16 h | 1:5 * |
2 | OMe | PXPd2 (1) | MeOH, reflux, 30 min | 2.5:1 * |
3 | NHCH2CH2OPh | PXPd2 (1) | MeOH, 55 °C, 1 h | 9:1 ** |
Entry | Ligand | Base | Solvent | Yield (%) | |
---|---|---|---|---|---|
35 | 36 | ||||
1 | DPPF | Cs2CO3 | dioxane | 0 | 90 |
2 | Q-Phos | KF | toluene | 36 | 15 |
3.3. Pyridazine Derivatives
3.4. Oxazole Derivatives
3.5. Imidazole Derivatives
4. Conclusions
Author Contributions
Conflicts of Interest
References
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Manabe, K.; Yamaguchi, M. Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes. Catalysts 2014, 4, 307-320. https://doi.org/10.3390/catal4030307
Manabe K, Yamaguchi M. Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes. Catalysts. 2014; 4(3):307-320. https://doi.org/10.3390/catal4030307
Chicago/Turabian StyleManabe, Kei, and Miyuki Yamaguchi. 2014. "Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes" Catalysts 4, no. 3: 307-320. https://doi.org/10.3390/catal4030307