A highly site-selective radical sp 3 C-H amination of azaheterocycles

This report describes the development of a novel C-H amination strategy using both a Cu(ii) Lewis acid and an organic hydrogen atom transfer catalyst to activate benzylic C-H bonds adjacent to aromatic N-heterocycles. This simple methodology demonstrates very high selectivity towards azaheterocycles...

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Bibliographic Details
Published inChemical science (Cambridge) Vol. 9; no. 30; pp. 6440 - 6445
Main Authors Bentley, Keith W, Dummit, Krysta A, Van Humbeck, Jeffrey F
Format Journal Article
LanguageEnglish
Published England 14.08.2018
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Summary:This report describes the development of a novel C-H amination strategy using both a Cu(ii) Lewis acid and an organic hydrogen atom transfer catalyst to activate benzylic C-H bonds adjacent to aromatic N-heterocycles. This simple methodology demonstrates very high selectivity towards azaheterocycles without using exogenous directing groups and affords excellent site selectivity in substrates with more than one reactive position. A wide range of heterocyclic structures not compatible with previously reported catalytic systems have proven to be amenable to this approach. Mechanistic investigations strongly support a radical-mediated H-atom abstraction, which explains the observed contrast to known closed-shell Lewis acid catalyzed processes.
ISSN:2041-6520
2041-6539
DOI:10.1039/C8SC00590G