The regioselective synthesis of variously substituted β-hydroxysulfones from thiosulfonates was developed. The reactions of thiosulfonates and alkenes via a peroxy radical intermediate provided 2° and 3° β-hydroxysulfones in good yields. The presence of epoxides instead of alkenes changed the reaction mechanism to nucleophilic addition involving sulfinate anions to afford 1° and 2° β-hydroxysulfones. By using both protocols, the regiochemical outcome of the β-hydroxysulfones synthesized from thiosulfonates was diversified.
This study was supported by the C1 refinery program (2015M3D3A1A01065436), the National Research Foundation of Korea (No. 2016R1D1A1A09917100), and the Ministry of Trade, Industry & Energy, Republic of Korea through the Human Resources Program in Energy Technology (No. 20154010200820) of the Korea Institute of Energy Technology Evaluation and Planning (KETEP).
