Imposing Latency in Ruthenium Sulfoxide-Chelated Benzylidenes: Expanding Opportunities for Thermal and Photoactivation in Olefin Metathesis

Gal Segalovich-Gerendash, Illya Rozenberg, Nebal Alassad, Noy B. Nechmad, Israel Goldberg, Sebastian Kozuch, N. Gabriel Lemcoff

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Herein we show the design and synthesis of an electron-rich, sulfoxide-chelated, ruthenium benzylidene. In contrast to previously reported sulfoxide-chelated ruthenium benzylidenes, this complex is more stable in a cis-dichloro conformation and is thus latent in typical olefin metathesis reactions. The complex was characterized by NMR, UV-vis, and X-ray spectroscopy, alongside density functional theory computations. The latent precatalyst could be activated thermally and, depending on the solvent, by UV-C or visible light. In addition, an original "thermo-chromatic" orthogonal sequence was developed, further improved by the use of a thioether chelated complex, where a divergent two-step synthesis can lead to a dihydrofuran or a dihydropyran depending only on the order by which the different stimuli, heat or light, are applied.

Original languageEnglish
Pages (from-to)4827-4834
Number of pages8
JournalACS Catalysis
Volume10
Issue number8
DOIs
StatePublished - 17 Apr 2020

Keywords

  • olefin metathesis
  • photoinduced
  • ruthenium
  • sulfoxide
  • sulfur-chelated

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)

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