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Bipyridine dearomatization vs. formation of imidazolyl ligands: dramatic effect of bipy substituents

AuthorsFombona, Sergio; Pérez, Julio ; Riera, Lucía
Issue Date2016
CitationXXXIV GEQO Congress (2016)
AbstractNew N-alkylimidazole (N-RIm; R= Me, Mes; Mes= mesityl, mesityl= 2,4,6-trimethylphenyl) complexes of the {Mo(η3-methallyl)(CO)2(4,4’-X2-bipy)} (η3-methallyl= η3-(2-methylallyl), 4,4’-X2-bipy= 4,4’-X2-2,2’-bipyridine) fragment have been prepared, in which the substituents of bipyridine are halogens (X= Cl, Br). The addition of a strong base to the new compounds deprotonates the central CH group of the imidazole ligand and subsequently an intramolecular nucleophilic attack affords a C-C coupling product with the bipy ligand in cis disposition. This reactivity contrasts with that previously found for the analogous nonsubstituted bipy, which afforded imidazol-2-yl complexes upon deprotonation. Therefore, this is the first report of bipy dearomatization in molybdenum complexes. The reaction of the dearomatized complexes with HOTf afforded immediately cationic species in which a CH group of the dearomatized pyridyl ring has been protonated generating a CH2 moiety. These new compounds have been characterized by infrared spectroscopy, nuclear magnetic resonance, elemental analysis and in some cases by X-ray diffraction. Furthermore, Density Functional Theory (DFT) computations have been carried out to understand the mechanism of the process.
DescriptionResumen del póster presentado al XXXIV GEQO Congress Organometallic Chemistry Group, celebrado en Girona (España) del 7 al 9 de septiembre de 2016.
Appears in Collections:(CINN) Comunicaciones congresos
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