DMSO/SOCl<sub>2</sub>-mediated C(sp<sup>2</sup>)–H amination: switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives
Jingran Zhang, Xiaoxian Li, Xuemin Li, Haofeng Shi, Fengxia Sun, Yunfei Du
Abstract
The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic methylthiolation.
Topics & Concepts
AminationIndole testChemistryMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryCatalysisSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsChemical Reactions and Isotopes