Copper-Catalyzed Bromination of C(sp3)−H Bonds Distal to Functional Groups

Tao Liu, Michael C. Myers, Jin-Quan Yu

Angew. Chem. Int. Ed.,
2016, Early View; DOI: 10.1002/ange.201608210


Selective bromination of γ-methylene C(sp3)−H bonds of aliphatic amides and δ-methylene C(sp3)−H bonds of nosyl-protected alkyl amines are developed using NBS as the brominating reagent and catalytic amount of CuII/phenanthroline complexes as the catalyst. Aryl and benzylic C−H bonds at other locations remain intact during this directed radical abstraction reaction.

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This work was supported by NSF under the CCI Center for Selective C–H Functionalization, CHE-1205646. Any opinions, findings, and conclusions or recommendations expressed here are those of the authors and do not necessarily reflect the views of the National Science Foundation (NSF).