Further studies on Ni/Zr-mediated one-pot ketone synthesis: Use of a mixture of NiI- And NiII-catalysts greatly improves the molar ratio of coupling partners

Atsushi Umehara, Yoshito Kishi

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A new Ni/Zr-mediated one-pot ketone synthesis is developed, with use of a mixture of (Me)3tpy·NiII- and py-(Me)imid·NiIICl2-catalysts. The NiI-catalyst selectively activates iodides, whereas the NiII-catalyst activates thio-pyridine esters. An adjustment of a relative loading of the two catalysts allows to tune the relative rate of the two activations and trap a short-lived radical intermediate(s) efficiently. Thus, the new method makes one-pot ketone synthesis highly effective even with a 1:1 mixture of the coupling partners. The synthetic value of the new method is demonstrated with the C-C bond formation at the final stage of a convergent halichondrin-synthesis.

Original languageEnglish
Pages (from-to)947-950
Number of pages4
JournalChemistry Letters
Volume48
Issue number8
DOIs
Publication statusPublished - 2019 Jan 1
Externally publishedYes

Keywords

  • Ketone coupling
  • Ni-catalyst
  • Zirconocene

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Further studies on Ni/Zr-mediated one-pot ketone synthesis: Use of a mixture of Ni<sup>I</sup>- And Ni<sup>II</sup>-catalysts greatly improves the molar ratio of coupling partners'. Together they form a unique fingerprint.

  • Cite this