Visible-Light-Induced Organobismuth(III)-Initiated Halogen-Atom Transfer for the Alkylation of Heterocycles with Unactivated Alkyl Iodides
Gaofeng Feng, Chao Zhang, Tao Cai, Chen Wang, Xuhong Wang, Yi-Sha Wang, Lemao Yu, Jian Jin
Abstract
as a new and sole XAT reagent, a visible-light-induced XAT-enabled protocol for the Minisci alkylation of heterocycles with unactivated iodoalkanes was disclosed. Broad substrate scope and practical applicability were demonstrated by 38 examples with up to 98% yield. Preliminary mechanistic investigations, including DFT calculations, demonstrated a radical pathway. This method features simple operation, no precaution against moisture and oxygen, and EtOH as a green solvent.
Topics & Concepts
ChemistryAlkylationAlkylScope (computer science)Substrate (aquarium)Combinatorial chemistryOrganic chemistryReaction conditionsSimple (philosophy)TRACE (psycholinguistics)CatalysisReagentRadical Photochemical ReactionsVanadium and Halogenation ChemistryOxidative Organic Chemistry Reactions