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“On-Water” Michael-Type Addition Reactions Promoted by PhSeZnCl

Authors

  • Benedetta Battistelli,

    1. Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy, Fax: +39-075-5855116
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  • Testaferri Lorenzo,

    1. Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy, Fax: +39-075-5855116
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  • Marcello Tiecco,

    1. Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy, Fax: +39-075-5855116
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  • Claudio Santi

    1. Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy, Fax: +39-075-5855116
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Abstract

In this communication we report that our reagent PhSeZnCl can be conveniently used to effect Michael addition like reactions of unsaturated ketones and electron-deficient alkynes, leading to synthetically useful β-seleno derivativesand vinyl selenides, respectively. The reactions are effected at room temperature in THF as well as under “on water” conditions. When the addition occurs on a triple bond, good stereoselectivity is observed, and the reaction shows a rate acceleration in water suspension.

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