Synthesis of 2,3-Dihydroselenophene and Selenophene Derivatives by Electrophilic Cyclization of Homopropargyl Selenides

详细信息    查看全文

• 作者：Ricardo F. Schumacher ; Alisson R. Rosrio ; Ana Cristina G. Souza ; Paulo H. Menezes ; Gilson Zeni
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：May 7, 2010
• 年：2010
• 卷：12
• 期：9
• 页码：1952-1955
• 全文大小：176K
• 年卷期：v.12,no.9(May 7, 2010)
• ISSN：1523-7052

文摘

The synthesis of several highly functionalized 2,3-dihydroselenophenes from homopropargyl selenides via electrophilic cyclization is described. Electrophiles such as I₂, ICl, and PhSeBr were used in a simple process employing CH₂Cl₂ as solvent at room temperature, which gave the cyclized products in high yields. 4-Iodo-2,3-dihydroselenophenes obtained by this methodology were submitted to a dehydrogenation reaction using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to give 3-iodoselenophenes. 4-Iodo-5-phenyl-2,3-dihydroselenophene was also submitted to the thiol copper-catalyzed and Heck-type reactions giving the desired products under mild reaction conditions.