Unprecedented Selectivity of Ruthenium Iodide Benzylidenes in Olefin Metathesis Reactions

Noy B. Nechmad, Ravindra Phatake, Elisa Ivry, Albert Poater, N. Gabriel Lemcoff

Research output: Contribution to journalArticlepeer-review

18 Scopus citations


The development of selective olefin metathesis catalysts is crucial to achieving new synthetic pathways. Herein, we show that cis-diiodo/sulfur-chelated ruthenium benzylidenes do not react with strained cycloalkenes and internal olefins, but can effectively catalyze metathesis reactions of terminal dienes. Surprisingly, internal olefins may partake in olefin metathesis reactions once the ruthenium methylidene intermediate has been generated. This unexpected behavior allows the facile formation of strained cis-cyclooctene by the RCM reaction of 1,9-undecadiene. Moreover, cis-1,4-polybutadiene may be transformed into small cyclic molecules, including its smallest precursor, 1,5-cyclooctadiene, by the use of this novel sequence. Norbornenes, including the reactive dicyclopentadiene (DCPD), remain unscathed even in the presence of terminal olefin substrates as they are too bulky to approach the diiodo ruthenium methylidene. The experimental results are accompanied by thorough DFT calculations.

Original languageEnglish
Pages (from-to)3539-3543
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number9
StatePublished - 24 Feb 2020


  • alkenes
  • olefin metathesis
  • ring-closing metathesis
  • ring-opening metathesis polymerization
  • ruthenium catalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)


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