FeCl3-diorganyl dichalcogenides promoted cyclization of 2-organochalcogen-3-alkynylthiophenes: synthesis of chalcogenophene[2,3-b]thiophenesElectronic supplementary information (ESI) available. See DOI: 10.1039/c3ob27498e
We report here our results on the FeCl 3 -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 obtai...
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Main Authors | , , , |
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Format | Journal Article |
Language | English |
Published |
17.04.2013
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Online Access | Get full text |
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Summary: | We report here our results on the FeCl
3
-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.
We present here our results on the FeCl
3
-diorganyl dichalcogenides intramolecular cyclization of 2-organochalcogen-3-alkynylthiophenes to prepare (S)-Se-, (S)-S- and (S)-Te-heterocycles. |
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Bibliography: | 10.1039/c3ob27498e Electronic supplementary information (ESI) available. See DOI |
ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/c3ob27498e |