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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

2020Science578 citationsDOIOpen Access PDF

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
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