Development of Pd-catalyzed denitrative couplings

Kitty K. Asahara, Myuto Kashihara, Kei Muto, Yoshiaki Nakao, Junichiro Yamaguchi

Research output: Contribution to journalArticlepeer-review

Abstract

Transition metal-catalyzed cross-coupling between aryl halides and nucleophiles is one of the most reliable C-C and C-heteroatom bond forming reactions. However, preparation of haloarenes usually requires multi-step operation, making the whole cross-coupling process inefficient. Nitroarenes, synthesized by a single-step nitration of arenes, can be attractive alternatives as electrophiles in cross-coupling methodology, but inherent inertness of C(sp 2)-NO 2 bonds toward metal catalysts has been a bottleneck of general denitrative transformations. Recently, we have overcome this obstacle and achieved direct activation of Ar-NO 2 bonds by using Pd/BrettPhos catalysis. Herein, we describe the development of denitrative couplings by Pd/BrettPhos catalyst and its unique suitability from a mechanistic point of view. Deep understanding of reaction mechanism also enabled us to design more active Pd/NHC system.

Original languageEnglish
Pages (from-to)11-21
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume79
Issue number1
DOIs
Publication statusPublished - 2021 Jan 1

Keywords

  • C-N bond cleavage
  • Coupling
  • Denitration
  • NHC ligand
  • Nitroarene
  • Palladium catalyst

ASJC Scopus subject areas

  • Organic Chemistry

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