Visible‐Light Promoted Stereoselective Arylselanyl Functionalization of Alkynes

Functionalization of double bonds with arylselenium groups found in the literature, commonly uses high temperatures in the presence of metal catalysts, reducing agents or other additives. In this context, this work presents a series of bis‐arylselanyl olefins synthesized by photoinduced reaction wit...

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Bibliographic Details
Published in:European journal of organic chemistry 2018-12, Vol.2018 (47), p.6738-6742
Main Authors: Weber, Andressa C. H., Coelho, Felipe L., Affeldt, Ricardo F., Schneider, Paulo H.
Format: Article
Language:English
Subjects:
Additives
Alkenes
Alkynes
Chemical synthesis
Dichloromethane
Environmental impact
Fluorescence
Fluorescent lamps
Isomerization
Photochemistry
Reagents
Reducing agents
Selenium
Stereoselective synthesis
Stereoselectivity
Visible light
White light
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Summary:Functionalization of double bonds with arylselenium groups found in the literature, commonly uses high temperatures in the presence of metal catalysts, reducing agents or other additives. In this context, this work presents a series of bis‐arylselanyl olefins synthesized by photoinduced reaction without heating or additives. Since the absorption range of the diselenide comprises the UV/Visible region of spectra, a mixture of arylacetylene and diaryl diselenide in dichloromethane was irradiated with white light from compact (household) fluorescent lamp. The optimized procedure allows preparation of E‐olefins due to radical addition followed by photoisomerization with low cost and low environmental impact. In this work a series of bis‐arylselanyl olefins were synthesized using visible white light from common fluorescent lamps as energy source, without catalyst or additives. The products were achieved in a very clean and fast way, yielding E‐olefins with good stereoselectivity, through radical addition‐photoisomerization.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201801303