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Synthesis of platinum complexes containing (+)-bornyl- and (−)-menthylammonium in the outer coordination sphere and their catalytic activity in hydrosilylation reactions

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Abstract

Optically active (+)-bornyl- and (−)-menthylammonium platinates were synthesized starting from H2[PtCl6] · 4H2O and hydrochlorides of the corresponding amines. Catalytic activity of the complexes in the hydrosilylation reactions of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane with 1,1,3,3-tetramethyldisiloxane and acetophenone with diphenylsilane was studied. The addition of the siloxanes leads to a predominant formation of β-adduct. Activity of the catalysts, evaluated on the 50% conversion of the substrate, decreases in the following sequence: (−)-(menthylNH3)2[PtCl6] > (Et3NH)2[PtCl6] > (+)-(bornylNH3)2[PtCl4] > (+)-(bornylNH3)2[PtCl6]. Asymmetric induction is observed in the hydrosilylation of aceto-phenone in the presence of (+)-(bornylNH3)2[PtCl n ] (n = 4, 6); (+)-(bornylNH3)2[PtCl6] showed the highest catalytic activity and selectivity. The hydrosilylation of acetophenone gave 1-phenylethoxy(diphenyl)silane, 1-phenylvinyloxy(diphenyl)silane, and 2-phenylethyl-2-diphenylsiloxy(diphenyl)silane as the products.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), 26 Moskovskii prosp., 190013, St. Petersburg, Russian Federation

    D. A. de Vekki, V. M. Uvarov, A. N. Reznikov & N. K. Skvortsov

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  1. D. A. de Vekki
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  2. V. M. Uvarov
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  3. A. N. Reznikov
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  4. N. K. Skvortsov
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Correspondence to D. A. de Vekki.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 341–349, February, 2008.

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de Vekki, D.A., Uvarov, V.M., Reznikov, A.N. et al. Synthesis of platinum complexes containing (+)-bornyl- and (−)-menthylammonium in the outer coordination sphere and their catalytic activity in hydrosilylation reactions. Russ Chem Bull 57, 349–357 (2008). https://doi.org/10.1007/s11172-008-0054-3

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  • DOI: https://doi.org/10.1007/s11172-008-0054-3

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