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Synthesis of Fused 4‐Iodoselenophene[2,3‐ b ]thiophenes by Electrophilic Cyclization of 3‐Alkynylthiophenes
Author(s) -
Stein André L.,
da Rocha Juliana,
Menezes Paulo Henrique,
Zeni Gilson
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901118
Subject(s) - chemistry , electrophile , reagent , palladium , combinatorial chemistry , electrophilic addition , coupling reaction , organic chemistry , catalysis , medicinal chemistry
We present here our results on the electrophilic cyclization reaction of 3‐alkynylthiophenes with different electrophiles such as I 2 , ICl, and PhSeBr. The cyclization reaction proceeded cleanly under mild reaction conditions, giving fused 4‐iodoselenophene[2,3‐ b ]thiophenes in excellent yields. In addition, the obtained chalcogenophenes were readily transformed into more complex products through palladium‐ or copper‐catalyzed cross‐coupling reactions with thiols, boronic acids, and organozinc reagents.