Sulfonyl Group-Induced Remote C(sp<sup>3</sup>)–N Bond Construction through Hydrogen Atom Transfer
Haotian Li, Xiancheng Qiu, Xu Zhang, Xinxin Wu
Abstract
This work demonstrates sulfonyl group-induced remote C(sp 3 )–N bond construction using a strategy of merging aryl radical-mediated halogen atom transfer and intramolecularly regioselective hydrogen atom transfer (HAT). A plethora of aliphatic sulfones, sulfonamides, and sulfonates are amenable and undergo regioselective C(sp 3 )–H amination by utilizing an iron salt at room temperature. This protocol involves iodine atom transfer, a HAT process enabled by an alkyl radical adjacent to a sulfonyl group, and amination mediated by an aryl diazonium salt.
Topics & Concepts
ChemistrySulfonylAminationRegioselectivityHalogenHydrogen atomAlkylArylSalt (chemistry)Medicinal chemistryAtom-transfer radical-polymerizationGroup (periodic table)Functional groupPhotochemistryOrganic chemistryCatalysisPolymerizationPolymerCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques