Exploring bis(cyclometalated) ruthenium(II) complexes as active catalyst precursors: Room-temperature alkene-alkyne coupling for 1,3-diene synthesis

Jing Zhang, Angel Ugrinov, Yong Zhang, Pinjing Zhao

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28 Scopus citations

Abstract

Described is the development of a new class of bis(cyclometalated) ruthenium(II) catalyst precursors for C-C coupling reactions between alkene and alkyne substrates. The complex [(cod)Ru(3-methallyl)2] reacts with benzophenone imine or benzophenone in a 1:2 ratio to form bis(cyclometalated) ruthenium(II) complexes (1). The imine-ligated complex 1a promoted room-temperature coupling between acrylic esters and amides with internal alkynes to form 1,3-diene products. A proposed catalytic cycle involves C-C bond formation by oxidative cyclization, β-hydride elimination, and C-H bond reductive elimination. This RuII/RuIV pathway is consistent with the observed catalytic reactivity of 1a for mild tail-to-tail methyl acrylate dimerization and for cyclobutene formation by [2+2] norbornene/alkyne cycloaddition.

Original languageEnglish
Pages (from-to)8437-8440
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number32
DOIs
StatePublished - 4 Aug 2014

Keywords

  • C-H activation
  • homogeneous catalyst
  • ligand effects
  • ruthenium
  • synthetic methods

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