Copper-Catalyzed Oxidative Benzylic C(sp3)−H Cyclization for the Synthesis of β-Lactams

Kanako Nozawa-Kumada, Satoshi Saga, Yuta Matsuzawa, Masahito Hayashi, Masanori Shigeno, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

β-Lactams are important structural motifs because of their ubiquity in natural products and pharmaceuticals. We report herein a Cu-catalyzed intramolecular oxidative C(sp3)−H amidation for the synthesis of β-lactams using tBuOOtBu. This method is based on Kharasch–Sosnovsky amidation and does not require prefunctionalization of C(sp3)−H bonds or the installation of a directing group, thereby allowing for the straightforward synthesis of β-lactams. Our intramolecular functionalization protocol can be extended to diverse benzylic C(sp3)−H bonds and shows excellent functional-group tolerance.

Original languageEnglish
Pages (from-to)4496-4499
Number of pages4
JournalChemistry - A European Journal
Volume26
Issue number20
DOIs
Publication statusPublished - 2020 Apr 6

Keywords

  • C(sp)−H functionalization
  • Kharasch–Sosnovsky reaction
  • beta-lactam
  • copper
  • oxidation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Copper-Catalyzed Oxidative Benzylic C(sp<sup>3</sup>)−H Cyclization for the Synthesis of β-Lactams'. Together they form a unique fingerprint.

Cite this