An Approach to the Selenobromination of Aryl(thienyl)alkynes: Access to 3‐Bromobenzo[b]selenophenes and Selenophenothiophenes. Issue 18 (7th May 2014)

• Record Type: Journal Article
• Authors: Paegle, Edgars; Belyakov, Sergey; Arsenyan, Pavel
• Is Part Of: European journal of organic chemistry. Issue 18(2014)
• Page Start: 3831
• Page End: 3840
• Publication Date: 2014-05-07
• Subjects: Heterocycles -- Selenophenes -- Selenium -- Bromination -- Cyclization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402095
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A novel approach for the cyclization of arylalkynes with selenium(IV) bromide prepared in situ has been elaborated. The use of an alkene additive as a bromine scavenger provides a convenient synthetic pathway for the synthesis of a wide variety of 3‐bromobenzo[ b ]selenophenes. Reactions can be performed open to air without the use of moisture‐sensitive reagents, anhydrous solvents, or an inert atmosphere. Selenobromination of ethynylthiophenes has been applied for the preparation of selenopheno[3, 2‐ b ]‐ and selenopheno[2, 3‐ b ]thiophenes. The molecular structures of representative derivatives have been confirmed by X‐ray crystallographic analysis. Abstract : The use of an alkene additive as a bromine scavenger under selenobromination conditions provides a convenient synthetic pathway for the synthesis of a wide variety of 3‐bromobenzo[ b ]selenophenes in moderate to high yields. The reactions are not moisture‐sensitive and do not require an inert atmosphere. Selenobromination of ethynylthiophenes enables the preparation of selenopheno[ b ]thiophenes.