Synthesis and Reactivity of 3‐Alkynyldihydroselenophene Derivatives

Abstract

Abstract 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.