Regioselective Formation of Tetrahydroselenophenes via 5-exo-dig-Cyclization of 1‑Butylseleno-4-alkynes

Results on the synthesis of tetrahydroselenophene derivatives from 1-butylseleno-4-alkynes by electrophilic cyclization using iodine as the electrophilic source are presented. This methodology was carried out via a simple process under mild reaction conditions providing the cyclized products in high...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2012-12, Vol.14 (23), p.6072-6075
Main Authors: Gai, Rafaela M, Schumacher, Ricardo F, Back, Davi F, Zeni, Gilson
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Hydrocarbons, Halogenated - chemical synthesis
Hydrocarbons, Halogenated - chemistry
Molecular Structure
Organoselenium Compounds - chemical synthesis
Organoselenium Compounds - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Results on the synthesis of tetrahydroselenophene derivatives from 1-butylseleno-4-alkynes by electrophilic cyclization using iodine as the electrophilic source are presented. This methodology was carried out via a simple process under mild reaction conditions providing the cyclized products in high yields. Electrophilic sources, such as PhSeBr, CuCl2, and CuBr2, were also used in this study. The tetrahydroselenophenes obtained by this protocol were submitted to cyanation, Suzuki, and Ullmann cross-coupling reactions to afford good yields of a cross-coupled product.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302919b