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Large-scale preparation and labelling reactions of deuterated silanes

Authors

  • Jesús Campos,

    1. Departamento de Química Inorgánica, Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla, Consejo Superior de Investigaciones Científicas, Avda. Américo Vespucio 49, Sevilla, Spain
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  • Miguel Rubio,

    1. Departamento de Química Inorgánica, Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla, Consejo Superior de Investigaciones Científicas, Avda. Américo Vespucio 49, Sevilla, Spain
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  • Ana C. Esqueda,

    1. Departamento de Química Inorgánica, Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla, Consejo Superior de Investigaciones Científicas, Avda. Américo Vespucio 49, Sevilla, Spain
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  • Ernesto Carmona

    Corresponding author
    • Departamento de Química Inorgánica, Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla, Consejo Superior de Investigaciones Científicas, Avda. Américo Vespucio 49, Sevilla, Spain
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Ernesto Carmona, Departamento de Química Inorgánica, Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla, Consejo Superior de Investigaciones Científicas, Avda. Américo Vespucio 49, 41092 Sevilla, Spain.

E-mail: guzman@us.es

Abstract

A catalytic synthesis of deuterated silanes SiEt3D, SiMe2PhD and SiPh2D2 is reported that allows their facile generation in a 3–4 g scale, utilizing D2 (0.5 bar) as the hydrogen isotope source and low catalyst loadings (0.01 mol%). The catalyst precursor is the rhodium (III) complex 1, which contains a (η5-C5Me5)Rh cation stabilized by coordination to a cyclometallated phoshine PMeXyl2 (Xyl = 2,6-C6H3Me2). The same complex is also an active catalyst for the hydrosilylation of the C[DOUBLE BOND]O and C≡N bonds of various ketones, aldehydes and α,β-unsaturated nitriles. Hence, combination of these two properties permits development of a simple and proficient one-flask, two-step procedure for the deuterosilylation of these substrates. Copyright © 2011 John Wiley & Sons, Ltd.

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