Synthesis of 2,3-dihydroselenophene and selenophene derivatives by electrophilic cyclization of homopropargyl selenides.
The synthesis of several highly functionalized 2,3-dihydroselenophenes from homopropargyl selenides via electrophilic cyclization is described. Electrophiles such as I(2), ICl, and PhSeBr were used in a simple process employing CH(2)Cl(2) 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.
Schumacher
Ricardo F
RF
Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, 97105-900, Santa Maria, RS, Brazil.
Rosário
Alisson R
AR
Souza
Ana Cristina G
AC
Menezes
Paulo H
PH
Zeni
Gilson
G
D003500:Cyclization; D018036:Selenium Compounds / Q000737:chemistry*
D018036:Selenium Compounds