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Paper | Special issue | Vol 97, No. 2, 2018, pp.806-822
Published online, 28th March, 2018
DOI: 10.3987/COM-18-S(T)56
Activation of Grubbs–Hoveyda Second-Generation Catalysts Employing Aromatic Ligands Bearing a Widespread Aryl Substituent

Yuki Kobayashi, Rina Igarashi, Yuta Ishikawa, Sae Inukai, Kento Shimowaki, Yuya Sugiyama, Takayuki Shioiri, and Masato Matsugi*

*Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya, Japan

Abstract

In this study, an activation strategy for Grubbs–Hoveyda second-generation-type catalysts by utilizing the intramolecular steric strain on the ligands is described. The variant, which is expected to exhibit intramolecular steric strain, containing extensively spread aromatic and alkoxy groups in the ligand structure was prepared and examined. The combination of tricyclic anthracenyl and isopropoxy groups are observed to exhibit the highest catalytic activity among these synthetic catalysts. The activated catalyst was successfully used in a ring-closing metathesis reaction depicting a catalyst loading of the order of 20 mol ppm in dry benzene. The X-ray crystallographic analysis suggests the existence of an intramolecular CH/π interaction between the sp2 carbon of the anthracenyl group and the methyne hydrogen of the isopropoxy group.