DES as a green solvent to prepare 1,2-bis-organylseleno alkenes. Scope and limitations

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• 作者：Eric F. Lopes^a ; Ló ; ren C. Gonç ; alves^a ; Julio C.G. Vinueza^a ; Raquel G. Jacob^a ; Gelson Perin^a ; Claudio Santi^b ; Eder J. Lenardã ; o^a ; ^{lenardao@ufpel.edu.br" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Organoselenium compounds ; Green chemistry ; Bis-chalcogen alkenes ; Deep eutectic solvent ; Alkynes
• 刊名：Tetrahedron Letters
• 出版年：2015
• 出版时间：9 December 2015
• 年：2015
• 卷：56
• 期：49
• 页码：6890-6895
• 全文大小：2780 K

文摘

We describe here our results on the use of choline chloride/urea 1:2 as a deep eutectic solvent (DES) in the synthesis of vinyl selenides. A good selectivity for the (E)-1,2-bis-organylseleno alkenes was observed starting from terminal alkynes and diaryl or dibutyl diselenides in the presence of NaBH₄. The reaction of 1,3-butadiynes with diphenyl diselenide afforded exclusively the respective mono-selenylated (Z)-alkenynes. Diphenyl ditelluride reacted with phenylacetylene and 1,4-diphenyl-but-1-en-3-yne affording (Z)-phenyltelluro alkenes in good yields.