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Molecules 2017, 22(3), 391;

Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes

Laboratório de Síntese Orgânica Limpa (LASOL), Centro de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, 96010-900 Pelotas, RS, Brazil
Department of Pharmaceutical Sciences, Group of Catalysis and Organic Green Chemistry, University of Perugia, Via del Liceo 1, 06100 Perugia, Italy
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 24 January 2017 / Revised: 22 February 2017 / Accepted: 28 February 2017 / Published: 2 March 2017
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Herein we describe the synthesis of organoselanyl and organotellanyl alkynes by the addition of lithium alkynylchalcogenolate (Se and Te) to tosyl solketal, easily obtained from glycerol. The alkynylchalcogenolate anions were generated in situ and added to tosyl solketal in short reaction times, furnishing in all cases the respective products of substitution in good yields. Some of the prepared compounds were deprotected using an acidic resin to afford new water-soluble 3-organotellanylpropane-1,2-diols. The synthetic versatility of the new chalcogenyl alkynes was demonstrated in the iodocyclization of 2,2-dimethyl-1,3-dioxolanylmethyl(2-methoxyphenylethynyl)selane 3f, which afforded 3-iodo-2-(2,2-dimethyl-1,3-dioxolanylmethyl) selenanylbenzo[b]furan in 85% yield, opening a new way to access water-soluble Se-functionalized benzo[b]furanes. View Full-Text
Keywords: selenium; tellurium; 1,3-dioxolanes; glycerol; alkynes selenium; tellurium; 1,3-dioxolanes; glycerol; alkynes

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Lenardão, E.J.; Borges, E.L.; Stach, G.; Soares, L.K.; Alves, D.; Schumacher, R.F.; Bagnoli, L.; Marini, F.; Perin, G. Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes. Molecules 2017, 22, 391.

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