EN300-43675

Reagent for aliphatic sulfonyl fluoride synthesis and promoter of Hoffman rearrangement

Phenyliodine(III) diacetate is a useful hypervalent Iodine reagent that can be used in various situations. It is a stable white solid that has good solubility in AcOH, MeCN, and CH2Cl2. By itself, the reagent is capable of undergoing various oxidation reactions, such as alcohol oxidation (with a catalytic amount of TEMPO[1]. Additionally, it has been employed in the oxidation of anilines to facilitate intramolecular azo group formation. Recently, innovative protocols have emerged[2], enabling the use of (Diacetoxyiodo)benzene in Hoffmann rearrangement reactions and the synthesis of aliphatic sulfonyl fluorides. The Hoffmann rearrangement protocol stands out for its metal-free, acid/base-free, and additive-free nature. It exhibits a broad substrate scope and excellent compatibility with various functional groups. Notably, this protocol can yield satisfactory results even when working with sterically hindered alkyl groups, such as isopropyl or adamantyl. The sulfonyl fluoride synthesis procedure offers a convenient one-pot reaction that can be executed either through a photocatalytic process or with moderate heating.