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Synthesis 2017; 49(16): 3662-3669
DOI: 10.1055/s-0036-1589032
DOI: 10.1055/s-0036-1589032
paper
Palladium-Catalyzed Oxidation-Hydroxylation and Oxidation-Methoxylation of N-Boc Indoles for the Synthesis of 3-Oxoindolines
This work was supported by the Union Foundation of Science and Technology Department of Guizhou Province (Grant No. qiankehe LH zi [2015] number 7614) and the High-Level Talents Start-up Foundation of Liupanshui Normal University (Grant No. LPSSYKYJJ201501).Further Information
Publication History
Received: 22 February 2017
Accepted after revision: 20 April 2014
Publication Date:
18 May 2017 (online)
Abstract
The palladium-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N-Boc indoles for the synthesis of tert-butyl 2-hydroxy(methoxy)-3-oxoindoline-1-carboxylates and their derivatives is developed. The process occurs readily using PdCl2 as the catalyst and acetonitrile as the solvent to afford 3-oxoindolines in moderate to high yields. A mechanism for this Pd-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N-Boc indoles is proposed.
Supporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589032.
- Supporting Information
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For Sigman’s work on Pd-catalyzed Wacker oxidation, see: