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Use of Hypervalent Iodine Reagents in Visible Light-Promoted α-Ketoacylations of Sulfoximines with Aryl Alkynes

Chenyang Wang, Ding Ma, Yongliang Tu, Carsten Bolm

2020Organic Letters39 citationsDOI

Abstract

In visible light, sulfoximidoyl-containing hypervalent iodine reagents react with aryl alkynes to give N-α-ketoacylated sulfoximines in good to high yields. The process is metal- and base-free, providing the diketonic products without the use of highly oxygenated reagents such as peroxides. Results from mechanistic investigations suggest the intermediacy of radicals and reveal the importance of molecular oxygen.

Topics & Concepts

Hypervalent moleculeChemistryReagentArylIodineRadicalCombinatorial chemistryBase (topology)Iodine compoundsVisible spectrumPhotochemistryOrganic chemistryAlkylPhysicsMathematical analysisOptoelectronicsMathematicsSynthesis and Catalytic ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods