Visible-light-mediated photoredox minisci C–H alkylation with alkyl boronic acids using molecular oxygen as an oxidant
Jianyang Dong, Fuyang Yue, Hongjian Song, Yuxiu Liu, Qingmin Wang
Abstract
Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation reactions of heteroarenes with alkyl boronic acids using molecular oxygen as the sole oxidant. This mild protocol uses an inexpensive, green oxidant; permits efficient functionalization of various N-heteroarenes with a broad range of primary and secondary alkyl boronic acids; and is scalable to the gram level. We demonstrated the practicality and sustainability of the protocol by preparing or functionalizing several pharmaceuticals and natural products.
Topics & Concepts
AlkylationAlkylChemistryBoronic acidPhotoredox catalysisVisible spectrumOxygenMolecular oxygenPhotochemistryCombinatorial chemistryOrganic chemistryMaterials scienceCatalysisPhotocatalysisOptoelectronicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions