Photoredox-catalyzed allylation of C(sp3)–H bonds in N-trifluoroethyl hydroxylamines or hydroxamides via hydrogen atom transfer

Abstract

Herein, we present an organophotoredox-catalyzed nitrogen-centered radical-triggered allylation reaction that enables the synthesis of trisubstituted alkenes from MBH adducts and N-trifluoroethylhydroxylamine reagents or hydroxamides via a hydrogen atom transfer (HAT) strategy. When N-trifluoroethylhydroxylamine reagents were employed as radical precursors, various homoallylic α-trifluoromethylamines were generated through 1,2-HAT of the in situ-generated N-trifluoroethyl radicals. Moreover, a series of hydroxamides (1,5-HAT reagents) could be tolerated by this catalytic system, affording the corresponding alkyl amides with excellent yields.