Abstract
Use of a tandem ring-opening-ring-closing metathesis (RORCM) strategy for the synthesis of functional metathesis catalysts is reported. Ring opening of 7-substituted norbornenes and subsequent ring-closing metathesis forming a thermodynamically stable 6-membered ring lead to a very efficient synthesis of new catalysts from commercially available Grubbs' catalysts. Hydroxy functionalized Grubbs' first- as well as third-generation catalysts have been synthesized. Mechanistic studies have been performed to elucidate the order of attack of the olefinic bonds. This strategy was also used to synthesize the ruthenium methylidene complex.
Highlights
Use of a tandem ring-opening–ring-closing metathesis (RORCM) strategy for the synthesis of functional metathesis catalysts is reported
Metathesis chemistry started with ill-defined catalysts,[3,4] but the development of well-defined metathesis catalysts provided an impetus to extensive applications in synthetic organic and polymer chemistry
There are mainly two metals used in metathesis catalysts: molybdenum-based complexes developed by the Schrock group, and rutheniumbased metathesis catalysts developed by the Grubbs group.[5]
Summary
Use of a tandem ring-opening–ring-closing metathesis (RORCM) strategy for the synthesis of functional metathesis catalysts is reported. The first generation and the third generation of Grubbs metathesis catalysts (Figure 1; G1 and G3) are the most common catalysts used for polymer synthesis owing to their favorable initiation/propagation rate ratio, which makes them suitable for living polymerizations. Fribourg (Switzerland) E-mail: andreas.kilbinger@unifr.ch terminate ring-opening metathesis polymerization (ROMP) reactions.
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