Synthesis of 2, 3-bis-organochalcogenyl-benzo[b]chalcogenophenes promoted by Oxone®. (3rd April 2019)

• Record Type: Journal Article
• Authors: Perin, Gelson; Soares, Liane K.; Hellwig, Paola S.; Silva, Marcio S.; Neto, José S. S.; Roehrs, Juliano A.; Barcellos, Thiago; Lenardão, Eder J.
• Is Part Of: New journal of chemistry. Volume 43:Number 16(2019)
• Page Start: 6323
• Page End: 6331
• Publication Date: 2019-04-03
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c9nj00526a
• Languages: English
• ISSNs: 1144-0546

Abstract

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®. 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.