Synthesis of 2,3-bis-organochalcogenyl-benzo[b]chalcogenophenes promoted by Oxone®†
Gelson
Perin, 
*a
Liane K.
Soares,
a
Paola S.
Hellwig,
a
Marcio S.
Silva,
a
José S. S.
Neto,
a
Juliano A.
Roehrs,
b
Thiago
Barcellos
c
and
Eder J.
Lenardão
*a
*a
Liane K.
Soares,
a
Paola S.
Hellwig,
a
Marcio S.
Silva,
a
José S. S.
Neto,
a
Juliano A.
Roehrs,
b
Thiago
Barcellos
c
and
Eder J.
Lenardão
*a
Abstract
We report here an alternative and tunable metal-free synthesis of benzo[b]chalcogenophenes via the electrophilic cyclization of 2-functionalized chalcogenoalkynes promoted by Oxone®. The use of mild reaction conditions, efficiency and generality are characteristics of this new approach, which was suitable to convert different diselenides and 2-functionalized chalcogenoalkynes into a total of twenty-two 2,3-bis-organochalcogenyl-benzo[b]chalcogenophenes, eighteen of which were synthesized for the first time. The new compound 2-(butylselanyl)-3-(phenylselanyl)benzofuran was used as a substrate in the Pd-catalyzed reaction with phenylacetylene to access the Sonogashira's coupling derivative in good yield.
![Graphical abstract: Synthesis of 2,3-bis-organochalcogenyl-benzo[b]chalcogenophenes promoted by Oxone®](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C9NJ00526A&imageInfo.ImageIdentifier.Year=2019)
- This article is part of the themed collection: Selenium & Tellurium chemistry at the beginning of the 3rd millennium: a celebration of ICCST
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