Sulfonyloxylation and Acetoxylation of Aryl C–H Proximal to a λ3-Iodanediyl Group on Biaryl Structures

Abstract

λ3-Iodane-mediated proximal aryl C–H sulfonyloxylation and acetoxylation on 2-iodo-1,1′-biphenyl structures have been achieved. Intramolecular electron transfer between cationic I(III) and proximal 2-Ar groups in 2-arylphenyl-λ3-iodanes is a key step to generate the iodanyl radical intermediate with a radical cationic Ar moiety that undergoes the nucleophilic addition of acetate or sulfonate. Electron spin resonance experiments supported the proposed mechanism. A 2-benzyl-iodobenzene structure was also applicable to this reaction system.