Iodine-Mediated Alkoxyselenylation of Alkenes and Dienes with Elemental Selenium

Author:

Kurkutov Evgeny O.ORCID,Shainyan Bagrat A.ORCID

Abstract

A one-pot synthesis of linear and cyclic β-alkoxyselenides is developed through the iodine-mediated three-component reaction of elemental selenium with alkenes (dienes) and alcohols. Selenylation of 1,5-hexadiene gives 2,5-di(methoxymethyl)tetrahydroselenophene and 2-methoxy-6-(methoxymethyl)tetrahydro-2H-selenopyran via the 5-exo-trig and 6-endo-trig cyclization. 1,7-Octadiene affords only linear 1:2 adduct with two terminal double bonds. 1,5-Cyclooctadiene results in one diastereomer of 2,6-dialkoxy-9-selenabicyclo [3.3.1]nonanes via 6-exo-trig cyclization. With 1,3-diethenyl-1,1,3,3-tetramethyldisiloxane, the first ring-substituted representative of a very rare class of heterocycles, 1,4,2,6-oxaselenadisilinanes, was obtained at a high yield.

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Reference38 articles.

1. Organoselenium Chemistry: Synthesis and Reactions,2012

2. Organoselenium Chemistry. Encyclopedia of Inorganic and Bioinorganic Chemistry,2018

3. Insights into the Recent Synthetic Advances of Organoselenium Compounds

4. “Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

5. Chemistry of Biologically Important Synthetic Organoselenium Compounds

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