FeCl3-diorganyl dichalcogenides promoted cyclization of 2-organochalcogen-3-alkynylthiophenes: synthesis of chalcogenophene[2,3-b] thiophenes

We report here our results on the FeCl3-diorganyl dichalcogenides intramolecular cyclization of 2-organochalcogen-3-alkynylthiophenes. The cyclization reaction proceeded cleanly under mild reaction conditions giving the (S)-Se-, (S)-S- and (S)-Te-heterocycles in good yields. In addition, the obtaine...

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Published inOrganic & biomolecular chemistry Vol. 11; no. 18; pp. 2972 - 2978
Main Authors Stein, Andre L., Bilheri, Filipe N., Rosario, Alisson R., Zeni, Gilson
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.05.2013
Subjects
Catalysis
Chalcogens - chemistry
Chemistry
Chemistry, Organic
Chlorides - chemistry
Cyclization
Ferric Compounds - chemistry
Lithium - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Palladium - chemistry
Physical Sciences
Science & Technology
Thiophenes - chemistry
DISELENIDES
TELLURIUM
CATALYZED REACTIONS
VERSATILE
LITHIUM-SELENIUM EXCHANGE
TANDEM REACTION
ALKYNES
DERIVATIVES
BENZOFURAN
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Summary:We report here our results on the FeCl3-diorganyl dichalcogenides intramolecular cyclization of 2-organochalcogen-3-alkynylthiophenes. The cyclization reaction proceeded cleanly under mild reaction conditions giving the (S)-Se-, (S)-S- and (S)-Te-heterocycles in good yields. In addition, the obtained chalcogenophenes were readily transformed into more complex products using the palladium cross-coupling reaction with boronic acids. Conversely, using a metal-halogen exchange reaction with n-BuLi, the chalcogenophenes produced the lithium-intermediate which was trapped with aldehyde furnishing the desired secondary alcohol in good yield.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob27498e