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Synteza i zastosowanie nowych katalizatorów metatezy olefin

Hryniewicka A.

Wiadomości Chemiczne

2014

[Z] 68, 11-12

961--980

Olefin metathesis has emerged as a powerful tool for the formation of carboncarbon double bonds. The success of this methodology has spurred the intense investigation of new catalysts showing a better application profile. The syntheses and the application profiles of the seven new ruthenium metathesis catalysts have been described. Five of them were modified in benzylidene part with 6-hydroxychromane- and 2H-3,4-chromenemethylidene moiety. In chromanol – α-tocopherol model compound, some specific stereoelectronic effects have been observed. Introduction of this ligand to the catalyst may provide new advantageous properties. The other new catalysts contained modified N-heterocyclic carbene ligand (NHC), in which N,N’-mesityl substituents of NHC system were linked with diethylene glycol chain as a “clamping ring”. This ring would contribute to a steric shield of the NHC and ruthenium coordination center. Probably it may inforce a proper orientation of substituents in metallacyclobutane (all-cis), leading to Z-olefin formation. The obtained catalysts were investigated in model reactions: ring closing metathesis, cross metathesis and enyne metathesis. The experiments proved they efficiency. In many reactions the catalysts showed activity comparable or superior to that of commercially available Grubbs and Hoveyda 2nd generation complexes. Stereochemistry Z/E of the cross-metathesis products obtained using new and known complexes were similar as well. The catalysts were applied in the synthesis of a new type of α-tocopherol glycoconjugates. An efficient method of the synthesis Hoveyda 2nd type complexes starting from ruthenium trichloride was developed. It is possible to circumvent using special laboratory equipment and expensive reagents. Hoveyda type complexes can be achieved with very good yield in gram scale. Keywords: