A simple and stereoselective synthesis of (Z)-1,2-bis-arylselanyl alkenes from alkynes using KF/Al₂O₃

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• 作者：Renata G. Lara ; Paloma C. Rosa ; Liane K. Soares ; Má ; rcio S. Silva ; Raquel G. Jacob ; Gelson Perin ; ^{gelson_perin@ufpel.edu.br}
• 关键词：Organoselenium compounds ; PEG-400 ; Vinyl selenides ; Microwave irradiation ; KF/Al2O3
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：23 December, 2012
• 年：2012
• 卷：68
• 期：51
• 页码：10414-10418
• 全文大小：585 K

文摘

The title compounds were synthesized by a one-pot reaction of diaryl diselenides with terminal alkynes avoiding the previous preparation of arylselanyl alkynes. The reactions were performed under mild conditions with a range of terminal alkynes using KF/Al₂O₃ and PEG-400 as solvent. The addition of diaryl diselenides to alkynes occurred stereoselectively to give exclusively (Z)-1,2-bis-arylselanyl alkenes in good yields. The reaction time was reduced to a few minutes using microwave irradiation and the KF/Al₂O₃/PEG-400 system can be reused one time without previous treatment with comparable activity.