ABSTRACT
A novel ammonium iodide-induced sulfenylation method of flavones, indole and arylimidazo[1,2-a]pyridines using stable and odorless sodium benzenesulfinates as sulfur sources was developed, generating regioselective derivatives in good yields. This method has enriched current thioether-producing methods and provided a good example of using ammonium iodide as a reaction inducer instead of iodine to make thioethers under environmentally friendly and odorless conditions.
ABSTRACT
A novel and highly regioselective ammonium iodide-induced nonradical sulfenylation method for the construction of a C-S bond was developed via C-H functionalization. With DMSO or R(1)SO2NHNH2 as a sulfenylating agent, MeS- and R(1)S-substituted flavone derivatives were obtained in good yields. This method enriches current C-S bond formation chemistry, making it a highly valuable and practical method in pharmaceutical industry.
Subject(s)
Flavones/chemistry , Quaternary Ammonium Compounds/chemistry , Sulfhydryl Compounds/chemistry , Ammonium Compounds , Catalysis , Hydrogen Bonding , Molecular StructureABSTRACT
Coumarin and flavone derivatives are highly valuable molecules in drug discovery. Here, two new regioselective cross-dehydrogenation couplings of coumarins and flavones with different ethers via C(sp(3))-H functionalization processes were developed, generating new ether-substituted derivatives not previously reported. These reactions proceeded well via radical mechanisms and provided the corresponding products in good yields.
