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Synlett 2018; 29(07): 969-973
DOI: 10.1055/s-0036-1591904
DOI: 10.1055/s-0036-1591904
letter
Palladium-Catalyzed Oxidation of Indoles to Isatins by tert-Butyl Hydroperoxide
This research is sponsored by the research funds of Ningbo University (No. ZX2016000748) and by the K. C. Wong Magna Fund of Ningbo University.Weitere Informationen
Publikationsverlauf
Received: 30. November 2017
Accepted after revision: 02. Januar 2018
Publikationsdatum:
31. Januar 2018 (online)
Abstract
The combination of a Pd catalyst and tert-butyl hydroperoxide (TBHP) is a powerful catalytic system for many types of oxidative transformations. Here, we report that a Pd/TBHP system facilitates the oxidation of indoles with a range of functionalities to give the corresponding isatin derivatives in good yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591904.
- Supporting Information
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- 17 1-Methyl-1H-indoline-2,3-dione (N-methylisatin, 2a); Typical Procedure A vial was charged with Pd(OAc)2 (0.05 mmol), N-methylindole 1a (0.5 mmol), 70% aq TBHP (1 mL), and MeCN (3.0 mL), and the mixture was stirred at 80 °C for 1 h. The reaction was then quenched with sat. aq Na2SO3 to remove residual TBHP, and the mixture was extracted with EtOAc (3×10 mL). The organic layer was separated, dried (Na2SO4), and concentrated. Flash column chromatographic purification [silica gel, EtOAc–PE, 5:1] gave a red solid; yield: 67 mg (83%). 1H NMR (400 MHz, CDCl3): δ = 7.60–7.53 (m, 2 H), 7.11 (t, J = 7.4 Hz, 1 H), 6.88 (d, J = 7.8 Hz, 1 H), 3.22 (s, 3 H). 13C NMR (101 MHz, CDCl3): δ = 183.3, 158.1, 151.3, 138.4, 125.1, 123.7, 117.3, 109.9, 26.1.