Practical Catalytic Cleavage of C(sp3)−C(sp3) Bonds in Amines

Wu Li, Weiping Liu, David K. Leonard, Jabor Rabeah, Kathrin Junge, Angelika Brückner, Matthias Beller

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

The selective cleavage of thermodynamically stable C(sp3)−C(sp3) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper-based catalysts in the presence of air. The utility of this novel methodology is demonstrated for Cα−Cβ bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules.

Original languageEnglish
Pages (from-to)10693-10697
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume58
Issue number31
DOIs
StatePublished - 29 Jul 2019
Externally publishedYes

Keywords

  • C−C cleavage
  • air
  • amines
  • copper
  • morpholines

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