Synthesis and catalysis of a Z-stereoretentive ruthenium carbene catalyst chelated by 2,4,5,7-tetrachloro-1,8-dimercaptonaphthalene for olefin metathesis?

New Journal of Chemistry Pub Date: 2022-03-17 DOI: 10.1039/D2NJ00025C

Abstract

In this work, a 2,4,5,7-tetrachloro-1,8-dimercaptonaphthalene ligand-chelated ruthenium-based carbene olefin metathesis catalyst was synthesized. The synthesized catalyst catalyzed the ring-opening cross-metathesis reactions of norbornene/exo,exo-5-norbornene-2,3-dimethanol with styrene/4-fluorostyrene to obtain high Z-products (97?:?3–99?:?1 Z/E). The cross-metathesis reactions of (Z)-2-butene-1,4-diol with terminal alkenes using the synthesized catalyst gave high Z-stereoretentive products (91?:?9–98?:?2 Z/E). Compared to the previously reported Ru catalysts with naphthalene-1,8-dithiolate and 1,2-dicarbadodecaborane (12)-1,2-dithiolate, the prepared Ru complex exhibited higher catalytic activity under similar catalytic conditions. In addition, the new catalyst tolerates various olefin substrates containing different functional groups.

Graphical abstract: Synthesis and catalysis of a Z-stereoretentive ruthenium carbene catalyst chelated by 2,4,5,7-tetrachloro-1,8-dimercaptonaphthalene for olefin metathesis
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