Issue 2, 2017

Iodine-mediated regioselective 5-endo-dig electrophilic cyclization reaction of selenoenynes: synthesis of selenophene derivatives

Abstract

Selenoenynes underwent electrophilic cyclization reactions with iodine in the presence of an appropriate nucleophile to give 3-iodo-selenophenes and 3-organoselenyl-selenophenes. The selection of the appropriate reaction conditions allowed the cyclization process, which involves the initial formation of an iodonium intermediate, followed by a regioselective 5-endo-dig intramolecular selenium nucleophilic attack to the carbon–carbon triple bond. The key step for the preparation of the desired selenophenes was the trap of an allylic cation intermediate by N- and O-nucleophiles. The generality and limitations of the reactions with regard to each of the substituents at the starting materials were evaluated and addressed. The resulting 3-iodo-selenophenes were further functionalized by Sonogashira and Suzuki cross-coupling reactions.

Graphical abstract: Iodine-mediated regioselective 5-endo-dig electrophilic cyclization reaction of selenoenynes: synthesis of selenophene derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
26 Aug 2016
Accepted
28 Nov 2016
First published
29 Nov 2016

Org. Chem. Front., 2017,4, 277-282

Iodine-mediated regioselective 5-endo-dig electrophilic cyclization reaction of selenoenynes: synthesis of selenophene derivatives

R. P. Pistoia, J. A. Roehrs, D. F. Back and G. Zeni, Org. Chem. Front., 2017, 4, 277 DOI: 10.1039/C6QO00491A

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