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Synthesis 2016; 48(10): 1541-1549
DOI: 10.1055/s-0035-1561402
DOI: 10.1055/s-0035-1561402
paper
Iron-Catalyzed One-Pot N-Aroylation of NH-Sulfoximines with Methylarenes through Benzylic C–H Bond Oxidation
Further Information
Publication History
Received: 08 October 2015
Accepted after revision: 11 February 2016
Publication Date:
22 March 2016 (online)
Abstract
An efficient catalytic method has been developed for the synthesis of N-aroylated sulfoximines from readily available toluenes (methylarenes) as source of the aroyl coupling partner and NH-sulfoximines, employing an environmentally benign iron catalyst. This protocol involves oxidation of benzylic C–H bonds of toluenes to generate aroyl radical intermediates followed by oxidative coupling with NH-sulfoximines to form N-aroylated sulfoximines in good to excellent yields. The intermediate aroyl radical is successfully trapped with TEMPO to prove the radical pathway of the reaction.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561402.
- Supporting Information
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