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

• DOI: 10.1021/ol1003753
• Publication Date: 2010-03-29T15:30:09Z
• Authors: Ricardo F. Schuma...; Alisson R. Rosário; Ana Cristina G. S...; Paulo H. Menezes; Gilson Zeni
• Keywords: Cyclization; Selenium Compounds; 01 natural sciences; 0104 chemical sciences

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 solvent at room temperature, which gave the cyclized products high yields. 4-Iodo-2,3-dihydroselenophenes obtained by this methodology submitted to dehydrogenation reaction using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) give 3-iodoselenophenes. 4-Iodo-5-phenyl-2,3-dihydroselenophene was also thiol copper-catalyzed Heck-type reactions giving desired under mild conditions.