Recent Progress Concerning the N-Arylation of Indoles
Abstract
:1. Introduction
2. Transition-Metal-Free N-Arylation of Indoles
3. Transition-Metal-Catalyzed N-Arylation of Indoles
3.1. Nickel-Catalyzed N-Arylation of Indoles
3.2. Palladium-Catalyzed N-Arylation of Indoles
3.3. Copper-Catalyzed N-Arylation of Indoles
3.4. Miscellaneous Transition-Metal-Catalyzed N–Arylation of Indoles
4. N-Arylated Indoles as Biologically Active Substances
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Entry | Conditions | No. of Examples | indoleFG | Ar/hetArFG |
---|---|---|---|---|
1 | CuO nano (5 mol%), 1,10-phen (50 mol%) KOH (2 equiv), DMSO, reflux, 24 h | 4 56–80% | – | Cl |
2 | Cu@CeO2 (5 mol%), 1,10-phen (50 mol%) KOH (2 equiv), DMSO, reflux, 24 h | 6 82–89% | – | Cl |
3 | PhI, CuO NFs@MP (15 mg/mmol) K2CO3 (1.5 equiv), DMF, 100 °C, 6 h | |||
4 | CuO NPs (10 mg/1 mmol of indole), TEA (2 equiv), DMF, reflux, 2 h | |||
5 | CNT–CuO (5 mol%), tBuONa (3 equiv), DMSO, 120 °C, 12 h | 21 42–95% | Cl, F | Cl, F, COMe, CO2Me, CN, CF3, 3,4-(CH2OCH2), NO2, SMe |
6 | CuO nano (5 mol%), K2CO3 (1 equiv), DMF, reflux, 8 h | 15 62–98% | Br, CN, NO2, OMe | NO2 |
7 | Copper-decorated OMMT (5 mol%), K2CO3 (2 equiv), DMSO, 130 °C, 6 h | 8 73–97% | CN | OH, NH2, |
Entry | Conditions | No. of Examples | indoleFG | Ar/hetArFG | |
---|---|---|---|---|---|
1 | CuI (15 mol%)/L1 (15 mol%) tBuOK (2 equiv), DMSO, 120 °C, 36–48 h | 25 50–93% | CH=O, OMe | NO2, OMe, | |
2 | CuI (2 mol%)/L2 (4 mol%) K2CO3 (2.5 equiv), DMSO, 90 °C | 19 31–98% | – | Cl, CF3, CN, COCH3, CO2H, F, NH2, NO2 | |
3 | CuI (5 mol%)/L-proline (10 mol%), K2CO3 (5 equiv) DMSO, 80–90 °C, 24 h | 18 51–97% | Br, Cl, F, MeO, | Br, Cl, F, OMe, OH | |
4 | CuI (5 mol%), L-methionine (10 mol%), K2CO3 (2 equiv), DMF, 100 °C, 24 h | 16 72–92% | Br, F, NO2, OBn, OMe, | F, CF3, NO2, | |
5 | CuI (10 mol%), L3 (20 mol%), Cs2CO3 (2 equiv), DMF, 130 °C, 3–24 h | 29 62–91% | CHO, NO2, OMe | Br, Cl, NO2, OMe | |
Entry | Conditions | No. of Examples | indoleFG | Ar/hetArFG | |
---|---|---|---|---|---|
1 | CuO (2 equiv), K2CO3 (2 equiv), pyridine, reflux, 2–3 d | 11 15–96% | Cl, F, CO2Et, OBn | CF3, F, OMe, | |
2 | CuI (10 mol%), DMEDA (20 mol%), Cs2CO3 (1 equiv) DMSO, 120 °C, 4 h | ||||
3 | CuI (10 mol%), DMEDA (20 mol%), K3PO4 (2 equiv), toluene, 110 °C, 24 h | 13 74–91% | Ph | Cl, CO2Et, F, OMe | |
4 | CuI (10 mol%), K3PO4 (3 equiv), DMEDA (20 mol%), toluene, 110 °C, 12 h |
Entry | Conditions | No. of Examples | indoleFG | Ar/hetArFG |
---|---|---|---|---|
1 | CuI (10 mol%), DMSO (1 equiv), K2CO3 (2 equiv), glycerol, 120 °C, 24 h | 12 65–92% | Br, NO2, OMe | Br, F, NO2, OMe |
2 | Cu (10 mol%), L1 (20 mol%), Cs2CO3 (3 equiv) DMSO-H2O (1:1), 100 °C, 12–24 h | |||
3 | Cu2O (10 mol%), L2 (20 mol%), Cs2CO3 (2 equiv), DMSO, 120 °C, 3–24 h | 15 86–97% | CH3, CHO | Cl, COMe, CO2Me, COCH2CO2Et OMe, NO2 |
Entry | Conditions | No. of Examples | indoleFG | Ar/hetArFG |
---|---|---|---|---|
1 | CuBr2 (10 mol%), L1 (10 mol%), D-glucose (10 mol%), tBuONa (2 equiv), TPGS-750-M (5 wt%), 50 °C, 24 h | 11 43–95% | Br, Cl, F, OMOM, CHO, OMe, CH2CN, Cl, NO2 OMe | NO2, OMe |
2 | CuI (10 mol%), L2 (20 mol%), K3PO4 (2 equiv), betaine (2 equiv.), water, 90 °C, 10 h | 10 57–95% | – | Br, Cl, COMe, F, NO2, OMe |
3 | CuI (5 mol%), L3 (10 mol%), KOH (2 equiv), DME-H2O (3:7), 95 °C, 20 h | 23 42–95% | Br, CN, COMe, NO2 | Br, Cl, I, OMe |
Entry | Conditions | No. of Examples | indoleFG | Ar/hetArFG |
---|---|---|---|---|
1 | Cu2O (10 mol%), L1 (4 mol%), Cs2CO3 (2 equiv), DMSO, 120 °C, 20 h | 6 72–95% | – | NO2, OMe |
2 | CuI (10 mol%), L2 (10 mol%), K2CO3 (2 equiv), DMSO, 120 °C, 4–16 h | 7 84–97% | – | NO2, OMe |
3 | CuI (10 mol%), L3 (10 mol%), K2CO3 (1.4 equiv), DMSO, 110 °C, 24 h | 4 69–99 | CHO | OMe |
4 | CuCl (8 mol%), L4 (16 mol%), NaOH (1 equiv), DMSO, 120 °C, 24 h | 8 25–98% | – | Br, Cl, OEt, OMe |
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Oeser, P.; Koudelka, J.; Petrenko, A.; Tobrman, T. Recent Progress Concerning the N-Arylation of Indoles. Molecules 2021, 26, 5079. https://doi.org/10.3390/molecules26165079
Oeser P, Koudelka J, Petrenko A, Tobrman T. Recent Progress Concerning the N-Arylation of Indoles. Molecules. 2021; 26(16):5079. https://doi.org/10.3390/molecules26165079
Chicago/Turabian StyleOeser, Petr, Jakub Koudelka, Artem Petrenko, and Tomáš Tobrman. 2021. "Recent Progress Concerning the N-Arylation of Indoles" Molecules 26, no. 16: 5079. https://doi.org/10.3390/molecules26165079