A highly site-selective radical sp3 C-H amination of azaheterocycles.
Chem Sci
; 9(30): 6440-6445, 2018 Aug 14.
Article
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| MEDLINE
| ID: mdl-30310574
ABSTRACT
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.
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MEDLINE
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En
Revista:
Chem Sci
Año:
2018
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Article
País de afiliación:
Estados Unidos