Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides
Timothée Constantin, Margherita Zanini, Alessio Regni, Nadeem S. Sheikh, Fabio Juliá, Daniele Leonori
Abstract
Amines as a gateway to alkyl radicals In recent years, photoredox catalysis driven by blue light has often been used to oxidize carbon centers adjacent to nitrogen. Constantin et al. now show that these aminoalkyl radicals can, in turn, conveniently strip iodine atoms from a variety of alkyl carbons. The new alkyl radicals that result readily undergo deuteration and couplings such as alkylation, allylation, and olefination. The upshot is that simple amines can replace more hazardous conventional reagents such as trialkyltin compounds in the homolytic activation and functionalization of halocarbons. Science , this issue p. 1021
Topics & Concepts
ChemistryRadicalAlkylHalogenTributyltin hydrideHalideArylHomolysisPhotochemistryRedoxChemoselectivityReactivity (psychology)Halogen bondCombinatorial chemistryOrganic chemistryCatalysisAlternative medicinePathologyMedicineRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods