- FeCl3-diorganyl dichalcogenides promoted cyclization of 2-organochalcogen-3-alkynylthiophenes: Synthesis of chalcogenophene[2,3-b] thiophenes
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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. The Royal Society of Chemistry 2013.
- Stein, Andre L.,Bilheri, Filipe N.,Rosario, Alisson R.,Zeni, Gilson
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supporting information
p. 2972 - 2978
(2013/07/26)
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- Synthesis of fused 4-Iodoselenophene[2,3-b]thiophenes by electrophilic cyclization of 3-alkynylthiophenes
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We present here our results on the electrophilic cyclization reaction of 3-alkynylthiophenes with different electrophiles such as I2, ICl, and PhSeBr. The cyclization reaction proceeded cleanly under mild reaction conditions, giving fused 4-iodoselenophene[2,3-b]thiophenes in excellent yields. In addition, the obtained chalcogenophenes were readily transformed into more complex products through palladium- or copper-catalyzed cross-coupling reactions with thiols, boronic acids, and organozinc reagents.
- Stein, Andre L.,Da Rocha, Juliana,Menezes, Paulo Henrique,Zeni, Gilson
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experimental part
p. 705 - 710
(2010/03/24)
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