Highly stereoselective method to prepare bis-phenylchalcogen alkenes via addition of chalcogenolate to phenylseleno alkynes

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• 作者：Gelson Perin ; ^{gelson_perin@ufpel.edu.br} ; ^{perin@pq.cnpq.br} ; Elton L. Borges ; Diego Alves
• 关键词：PEG-400 ; Vinyl chalcogenides ; Bis-chalcogenides
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：18 April, 2012
• 卷：53
• 期：16
• 页码：2066-2069
• 文件大小：600 K

摘要

The preparation of bis-phenylchalcogen alkenes starting from phenylseleno alkynes is described. The nucleophilic species of selenium, tellurium and sulfur were generated in situ from the reaction of the respective diphenyl dichalcogenide with NaBH₄ in PEG-400 as solvent. The chalcogenolate anions were efficiently and selectively added to a variety of phenylselenoalkynes at mild conditions, furnishing the respective (Z)-1,2-bis-phenylchalcogen alkenes in good yields.