Iron-Catalyzed One-Pot N-Aroylation of NH-Sulfoximines with Methylarenes through Benzylic C-H Bond Oxidation
Madithedu Muneeswara, Surya Srinivas Kotha, Govindasamy Sekar*
*Department of Chemistry, Indian Institute of Technology
Madras, Chennai, Tamil Nadu 600 036, India, Email: gsekar
iitm.ac.in
M. Muneeswara, S. S. Kotha, G. Sekar, Synthesis, 2016, 48, 1541-1549.
DOI: 10.1055/s-0035-1561402
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Abstract
In an efficient synthesis of N-aroylated sulfoximines, methylarenes serve as aroyl coupling partner of NH-sulfoximines in the presence of 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. The intermediate aroyl radical is successfully trapped with TEMPO to prove the radical pathway of the reaction.
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Key Words
iron, oxidation, amides, sulfoximines, cross-coupling, radical reaction
ID: J66-Y2016
