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Molecules 2017, 22(3), 391; doi:10.3390/molecules22030391

Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes

1
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
2
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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Abstract

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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MDPI and ACS Style

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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