title: Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes.
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)selane3f, 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.
authors.affiliation: Laboratório de Síntese Orgânica Limpa (LASOL), Centrop de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, 96010-900 Pelotas, RS, Brazil. lenardao@ufpel.edu.br.
authors.forename: Eder J
authors.initials: EJ
authors.lastname: Lenardão
authors.affiliation: Laboratório de Síntese Orgânica Limpa (LASOL), Centrop de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, 96010-900 Pelotas, RS, Brazil. chemistry_borges@yahoo.com.br.
authors.forename: Elton L
authors.initials: EL
authors.lastname: Borges
authors.affiliation: Laboratório de Síntese Orgânica Limpa (LASOL), Centrop de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, 96010-900 Pelotas, RS, Brazil. guilherme.stach13@gmail.com.
authors.forename: Guilherme
authors.initials: G
authors.lastname: Stach
authors.affiliation: Laboratório de Síntese Orgânica Limpa (LASOL), Centrop de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, 96010-900 Pelotas, RS, Brazil. lianekrolowsoares@yahoo.com.br.
authors.forename: Liane K
authors.initials: LK
authors.lastname: Soares
authors.affiliation: Laboratório de Síntese Orgânica Limpa (LASOL), Centrop de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, 96010-900 Pelotas, RS, Brazil. dsalves@gmail.com.
authors.forename: Diego
authors.initials: D
authors.lastname: Alves
authors.affiliation: Laboratório de Síntese Orgânica Limpa (LASOL), Centrop de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, 96010-900 Pelotas, RS, Brazil. ricardo.schumacher@ufpel.edu.br.
authors.forename: Ricardo F
authors.initials: RF
authors.lastname: Schumacher
authors.affiliation: Department of Pharmaceutical Sciences, Group of Catalysis and Organic Green Chemistry, University of Perugia, Via del Liceo 1, 06100 Perugia, Italy. luana.bagnoli@unipg.it.
authors.forename: Luana
authors.initials: L
authors.lastname: Bagnoli
authors.affiliation: Department of Pharmaceutical Sciences, Group of Catalysis and Organic Green Chemistry, University of Perugia, Via del Liceo 1, 06100 Perugia, Italy. i@unipg.it.
authors.forename: Francesca
authors.initials: F
authors.lastname: Marini
authors.affiliation: Laboratório de Síntese Orgânica Limpa (LASOL), Centrop de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, 96010-900 Pelotas, RS, Brazil. gelson_perin@ufpel.edu.br.
authors.forename: Gelson
authors.initials: G
authors.lastname: Perin
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002625:Chemistry, Organic; D005990:Glycerol / Q000737:chemistry*; D055601:Organic Chemistry Phenomena; D009942:Organometallic Compounds / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D009942:Organometallic Compounds; D016566:Organoselenium Compounds; D005990:Glycerol
keywords: 1,3-dioxolanes; alkynes; glycerol; selenium; tellurium