Affiliation:
1. LCC-CNRS Université de Toulouse, CNRS 205 route de Narbonne. 31077 Toulouse cedex 4 France
2. Biological and Chemical Research Centre Faculty of Chemistry University of Warsaw Żwirki i Wigury Street 101 02-089 Warsaw Poland
3. Centre of New Technologies University of Warsaw S. Banacha 2c 02-097 Warsaw (Poland)
Abstract
AbstractThree Hoveyda‐Grubbs complexes supported by N‐(9‐alkylfluorenyl)imidazol‐2‐ylidene ligands (alkyl=methyl, ethyl or benzyl) have been synthesized. With the aim to generate chelating, cyclometalated (C,CNHC) ruthenium complexes for Z‐selective olefin metathesis, the C(sp3)‐H activation of the dangling alkyl group has been studied. While the methyl derivative leads to the expected cyclometalated complex, a C(sp2)‐H activation of the fluorenyl moiety and no evolution/transformation are observed for the ethyl and benzyl derivatives, respectively. Although highly fragile under catalytic conditions, the cyclometalated complex leads to Z/E stereoselectivity up to 94/6. An unprecedented insertion of the alkylidene moiety into the Ru‐CNHC bond leading to ruthenium N‐heterocyclic olefin complexes is also observed and supported by calculations of the corresponding reaction pathway.
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