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Synlett 2016; 27(18): 2621-2625
DOI: 10.1055/s-0035-1562537
DOI: 10.1055/s-0035-1562537
letter
Ruthenium-Catalyzed Intramolecular Cyclization and Fluorination to Form 3-Fluorooxindoles
Further Information
Publication History
Received: 18 May 2016
Accepted after revision: 23 July 2016
Publication Date:
10 August 2016 (online)
Abstract
We have developed a new and simple method for the preparation of 3-fluorooxindoles via synergetic cyclization and fluorination of α-diazoacetamides in the presence of [Ru(p-cymene)Cl2]2 under mild conditions. Two-step tandem processes include intramolecular cyclization followed by electrophilic fluorination with Selectfluor in one-pot.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562537.
- Supporting Information
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- 14 Typical Procedure of Ruthenium-Catalyzed Intramolecular Cyclization and Fluorination to Form 3-Fluorooxindoles The flame-dried round-bottomed flask was charged with Ru(p-cymene)Cl2]2 (6.2 mg, 2.5 mol%), Selecfluor (0.48 mmol, 1.2 equiv), and α-diazoacetamide 1a (0.4 mmol), and then was sealed. The flask was evacuated and backfilled with argon three times. Dry xylene (4 mL) and water (144 μL, 20 equiv) were added using a syringe. The mixture was stirred at 40 °C until the substrate disappeared as judged by TLC. After cooling to room temperature, the crude mixture was poured into water (20 mL). The residue was extracted with EtOAc and dried over Na2SO4. After filtration and evaporation in vacuo, the residue was purified by flash chromatography on silica gel (PE–EtOAc = 20:1) to give 2a as white solid (67.6 mg, 89%). 1H NMR (400 MHz, CDCl3): δ = 7.62 (dd, J = 7.5, 1.7 Hz, 1 H), 7.56 (t, J = 7.9 Hz, 1 H), 7.24 (t, J = 7.6 Hz, 1 H), 6.95 (d, J = 7.9 Hz, 1 H), 3.26 (s, 3 H). 19F NMR (376 MHz, CDCl3): δ = –152.56. 13C NMR (100 MHz, CDCl3): δ = 164.6 (d, J = 22.0 Hz), 144.3 (d, J = 4.7 Hz), 134.1 (d, J = 3.4 Hz), 126.2, 124.4 (d, J = 2.9 Hz), 120.3 (d, J = 20.1 Hz), 112.8 (d, J = 41.0 Hz), 109.9 (d, J = 1.5 Hz), 81.6 (d, J = 196.5 Hz), 27.0. ESI-MS: m/z [M + H]+ = 191.0.