Homolytic Aromatic Sulfonation with K<sub>2</sub>S<sub>2</sub>O<sub>5</sub> Promoted by a Combination of Mn(OAc)<sub>3</sub>·2H<sub>2</sub>O and HFIP
Bingxu Han, Xin Gu, Ke Li, Yun‐Kun Qi, Shuai Liang
Abstract
Herein, we reported a so far unprecedented Mn(OAc)3·2H2O-promoted homolytic aromatic sulfonation. The reaction was performed under mild conditions with K2S2O5 employed as a green sulfonating reagent. Various arenes were successfully converted into desired sulfonic acids or sulfonates in high efficiency. Preliminary mechanistic studies demonstrated that the present reaction proceeds via a homolytic aromatic substitution-type mechanism involving an SO3– radical. The combination of Mn(OAc)3·2H2O and HFIP plays a crucial role.
Topics & Concepts
HomolysisChemistryElectrophilic aromatic substitutionReagentMedicinal chemistryReaction mechanismReaction conditionsRadicalOrganic chemistryCatalysisSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsOrganic and Inorganic Chemical Reactions