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Site-Selective C–H Alkylation of Piperazine Substrates via Organic Photoredox Catalysis

Joshua B. McManus, Nicholas P. R. Onuska, Matthew S. Jeffreys, Nicole C. Goodwin, David A. Nicewicz

2020Organic Letters73 citationsDOI

Abstract

Piperazine-containing compounds serve as one of the most important classes of compounds throughout all fields of chemistry. Alas, current synthetic methods have fallen short of providing a general method for the synthesis of highly decorated piperazine fragments. Herein, we present a site-selective approach to the C-H functionalization of existing piperazine compounds using photoredox catalysis. This manifold relies on the predictable differentiation of electronically distinct nitrogen centers within the piperazine framework, granting access to novel C-alkylated variants of the starting piperazines.

Topics & Concepts

PiperazineChemistryAlkylationPhotoredox catalysisCatalysisCombinatorial chemistrySurface modificationOrganic chemistryPhotocatalysisPhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSynthesis and Catalytic Reactions
Site-Selective C–H Alkylation of Piperazine Substrates via Organic Photoredox Catalysis | Litcius