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AbstractReaction of 8-bromo-7-ethyl-3-methylxanthine 1 with zerovalent group 10 metal complexes gave via an oxidative addition of the C–Br bond the neutral complexes trans-[2] (M = Pd) and trans-[3] (M = Pt) bearing a theobromine-derived azolato ligand. While the oxidative addition to [Pd0(PPh3)4] gave exclusively trans-[2], the reaction with the more substitution-inert [Pt0(PPh3)4] yielded after 1 day the kinetic product cis-[3], which was converted under heating for a total of 3 days completely into the thermodynamically more stable complex trans-[3]. Treatment of trans-[2], trans-[3] or the mixture of cis-/trans-[3] with the proton source HBF4⋅Et2O led to complexes trans-[4]BF4, trans-[5]BF4 and a mixture of cis/trans-[5]BF4 with retention of the original ratio of cis to trans, respectively. The molecular structures of the azolato complexes trans-[2] and trans-[3] and of the theobromine derived pNHC complexes trans-[4]BF4 and trans-[5]BF4 have been determined by X-ray diffraction studies.
Zeitschrift für Naturforschung B – de Gruyter
Published: Apr 27, 2021
Keywords: N-heterocyclic carbene; oxidative addition; palladium; platinum
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