ChemInform Abstract: A General and Highly Efficient Protocol for the Synthesis of Chalcogenoacetylenes by Copper(I)‐Terpyridine Catalyst.

Movassagh, Barahman; Yousefi, Ali Akbar; Momeni, Badri Z.; Heydari, Sepideh

doi:10.1002/chin.201449193

Cited by 2 publications

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“…Additionally, chalcogenyl alkynes are useful in electrophilic cyclization reactions to prepare benzo[ b ]furans [ 20 ], in [4 + 2]-cycloadditions to produce the corresponding 2-chalcogenyl-1-halonaphthalenes [ 21 ], and in the synthesis of bis-phenylchalcogen alkenes [ 22 , 23 ]. Despite all the advances in this area, most of the papers are restricted to the synthesis of chalcogenyl alkynes starting mainly from aromatic terminal alkynes [ 24 , 25 , 26 , 27 , 28 , 29 , 30 ], with only a few methods to prepare aliphatic alkynylselenides and tellurides with different chalcogen substitution patterns.…”

Section: Introductionmentioning

confidence: 99%

Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes

et al. 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.

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