Copper-catalyzed site-selective intramolecular amidation of unactivated C(sp3)-H bonds

Xuesong Wu, Yan Zhao, Guangwu Zhang, Haibo Ge

Research output: Contribution to journalArticle

151 Scopus citations

Abstract

The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp3 C-H bond functionalization process. The reaction favors predominantly the C-H bonds of β-methyl groups over the unactivated methylene C-H bonds. Moreover, a preference for activating sp3 C-H bonds of β-methyl groups, via a five-membered ring intermediate, over the aromatic sp2 C-H bonds was also observed in the cyclometalation step. Additionally, sp3 C-H bonds of unactivated secondary sp3 C-H bonds could be functionalized by favoring the ring carbon atoms over the linear carbon atoms. Getting ahead on tams: The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp 3 C-H bond functionalization process to deliver β-lactams. The reaction favors the C-H bonds of β-methyl groups over the unactivated methylene C-H bonds, as well as aromatic C(sp2)-H bonds and unactivated secondary C(sp3)-H bonds of rings.

Original languageEnglish
Pages (from-to)3706-3710
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number14
DOIs
StatePublished - Apr 1 2014

Keywords

  • C-H activation
  • copper
  • heterocycles
  • homogeneous catalysis
  • synthetic methods

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