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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
Authors
This research is sponsored by the research funds of Ningbo University (No. ZX2016000748) and by the K. C. Wong Magna Fund of Ningbo University.
Further Information
Publication History
Received: 30 November 2017
Accepted after revision: 02 January 2018
Publication Date:
31 January 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 (PDF)
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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.