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Synlett 2025; 36(09): 1257-1261
DOI: 10.1055/a-2508-0449
DOI: 10.1055/a-2508-0449
letter
Arylation of Aldehydes with Indoles Using 1,3-Diisopropylimidazolinium Tetrafluoroborate as a Recyclable Catalyst for the Synthesis of Bis(indolyl)methanes in Water
This work was financially supported by the Yunnan Provincial Science and Technology Department–Applied Basic Research Joint Special Funds of Yunnan University of Chinese Medicine (202101AZ070001-238, 202301AZ070001-061).
Abstract
Bis(indolyl)methanes have attracted considerable attention for their interesting biological activities. Green organic-catalytic synthesis has promoted the development of green chemistry, especially in aqueous-phase reaction systems. We have developed a green and efficient catalytic arylation of aldehydes with indoles using low-cost 1,3-diisopropylimidazolinium tetrafluoroborate as a recyclable and reusable catalyst for the synthesis of bis(indolyl)methanes in water.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2508-0449.
- Supporting Information
Publication History
Received: 18 November 2024
Accepted after revision: 23 December 2024
Accepted Manuscript online:
23 December 2024
Article published online:
28 January 2025
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- 16 IiPrim·HBF4 NH4BF4 (624 mg, 6 mmol) was added to a stirred solution of N,N′-diisopropylethylenediamine (719 mg, 5 mmol) and triethyl orthoformate (740 mg, 5 mmol) in EtOH (20 mL), and the mixture was refluxed overnight. When the reaction was complete (TLC), the mixture was concentrated in vacuo. H2O (100 mL) was added to the residue and the mixture was extracted with CH2Cl2 (50 mL). The organic layer was dried and concentrated in vacuo to give a colorless solid. Purity (HPLC): >97%. 1H NMR (400 MHz, DMSO-d 6): δ = 8.41 (s, 1 H), 3.82–3.88 (m, 6 H), 1.25 (d, J = 8.0 Hz, 12 H). BIMs; General Procedure IiPrim·HBF4 (0.1 mmol) was added to a stirred solution of the appropriate indole or N-methylindole (0.5 mmol) and aldehyde (0.3 mmol) in H2O (2 mL), and the mixture was stirred at 80 °C for 1–3 h. When the reaction was complete (TLC), the mixture was diluted with EtOAc (5 mL) and the organic layer was dried and concentrated in vacuo. The residue was purified by column chromatography. 3,3′-(Phenylmethylene)bis-1H-indole (1a) White solid; yield: 91%. 1H NMR (400 MHz, CDCl3): δ = 7.79 (s, 2 H), 7.44 (d, J = 7.4 Hz, 2 H), 7.40 (d, J = 7.4 Hz, 2 H), 7.30–7.36 (m, 4 H), 7.24–7.27 (m, 3 H), 7.07 (t, J = 7.8 Hz, 2 H), 6.63 (s, 2 H), 5.92 (s, 1 H). 13C NMR (100 MHz, CDCl3): δ = 144.13, 136.69, 128.73, 128.25, 127.06, 126.02, 123.10, 121.33, 119.87, 119.73, 119.22, 110.87, 40.19.