Journal
CHEMISTRY LETTERS
Volume 52, Issue 2, Pages 79-83Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/cl.220488
Keywords
Hypervalent iodine; Sulfonyloxylation; Hypervalent Acetoxylation
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Proximal aryl C-H sulfonyloxylation and acetoxylation on 2-iodo-1,1-biphenyl structures have been achieved using λ3-iodane as a catalyst. The key step in this reaction involves intramolecular electron transfer between cationic I(III) and proximal 2-Ar groups in 2-arylphenyl-lambda 3-iodanes, leading to the generation of an iodanyl radical intermediate with a radical cationic Ar moiety. This intermediate then undergoes nucleophilic addition of acetate or sulfonate. The proposed mechanism is supported by electron spin resonance experiments. A 2-benzyl-iodobenzene structure is also compatible with this reaction system.
lambda 3-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-lambda 3-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.
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