General Chemoselective Suzuki-Miyaura Coupling of Polyhalogenated Aryl Triflates Enabled by an Alkyl-Heteroaryl-Based Phosphine Ligand

Chau Ming So (Corresponding Author), On Ying Yuen, Shan Shan Ng, Zicong Chen

Research output: Journal article publicationJournal articleAcademic researchpeer-review

1 Citation (Scopus)

Abstract

This study describes a general chemoselective Suzuki-Miyaura coupling of polyhalogenated aryl triflates with the reactivity order of C-Cl > C-OTf using a Pd/L33 catalyst. The methine hydrogen and the steric hindrance offered by the alkyl bottom ring of L33 were found to be key factors in reactivity and chemoselectivity. With the Pd/ L33 catalyst, a wide range of polyhalogenated (hetero)aryl triflates, which were independent of the substrates and of the relative positioning of the competing reaction sites, coupled well with (hetero)aryl, alkenyl, and alkylboronic acids to obtain the corresponding products with good chemoselectivity and yields. The chemoselective reaction could easily be scaled up to the gram scale, and the use of parts per million levels of Pd catalyst (as low as 10 ppm Pd) was achieved.

Original languageEnglish
Pages (from-to)7820-7827
Number of pages8
JournalACS Catalysis
Volume11
Issue number13
DOIs
Publication statusPublished - 2 Jul 2021

Keywords

  • chemoselectivity
  • palladium
  • phosphine
  • polyhalogenated aryl triflates
  • Suzuki−Miyaura coupling

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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