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Synthesis and Reactivity of 3‐Alkynyldihydroselenophene Derivatives
Author(s) -
Rosário Alisson R.,
Schumacher Ricardo F.,
Gay Bibiana M.,
Menezes Paulo H.,
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.201000588
Subject(s) - chemistry , sonogashira coupling , intramolecular force , chalcogen , reactivity (psychology) , palladium , combinatorial chemistry , oxidative coupling of methane , functional group , medicinal chemistry , organic chemistry , catalysis , polymer , alternative medicine , pathology , medicine
We present herein our results on the synthesis of 3‐alkynyldihydroselenophenes by palladium‐catalyzed Sonogashira cross‐coupling of 3‐iododihydroselenophenes with different alkynes under mild conditions in good to excellent yields. The developed protocol tolerated a wide range of functional groups in the dihydroselenophenes and alkynes. These 3‐alkynyldihydroselenophenes, bearing the chalcogen group, underwent highly selective intramolecular cyclizations when treated with I 2 to afford fused dihydroselenophene[2,3, b ]selenophene rings. In addition, 3‐alkynyldihydroselenophene obtained by this methodology was also submitted to an oxidative reaction by using DDQ to give the aromatic selenophene in moderated yields.