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Oxidative addition of a 8-bromotheobromine derivative to d10 metals

Oxidative addition of a 8-bromotheobromine derivative to d10 metals 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Zeitschrift für Naturforschung B de Gruyter

Oxidative addition of a 8-bromotheobromine derivative to d10 metals

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Publisher
de Gruyter
Copyright
© 2021 Walter de Gruyter GmbH, Berlin/Boston
ISSN
0932-0776
eISSN
1865-7117
DOI
10.1515/znb-2021-0011
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Zeitschrift für Naturforschung Bde Gruyter

Published: Apr 27, 2021

Keywords: N-heterocyclic carbene; oxidative addition; palladium; platinum

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