Gold(I)-catalyzed rearrangement of 3-silyloxy-1,5-enynes: an efficient synthesis of benzo[b]thiophenes, dibenzothiophenes, dibenzofurans, and indole derivatives
With the IPr ligand (IPr=1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene) on gold(I) excellent yields in the benzanellation of 2-substituted thiophenes, benzothiophenes, pyrroles, benzofurans, and indoles were achieved. The 1-siloxybut-3-ynyl side chains, incorporated in the anellation, are easily...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
19 April 2012
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| In: |
Chemistry - a European journal
Year: 2012, Volume: 18, Issue: 21, Pages: 6576-6580 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201200314 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/chem.201200314 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201200314 
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| Author Notes: | A. Stephen K. Hashmi, Weibo Yang, and Frank Rominger |
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| 245 | 1 | 0 | |a Gold(I)-catalyzed rearrangement of 3-silyloxy-1,5-enynes |b an efficient synthesis of benzo[b]thiophenes, dibenzothiophenes, dibenzofurans, and indole derivatives |c A. Stephen K. Hashmi, Weibo Yang, and Frank Rominger |
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| 520 | |a With the IPr ligand (IPr=1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene) on gold(I) excellent yields in the benzanellation of 2-substituted thiophenes, benzothiophenes, pyrroles, benzofurans, and indoles were achieved. The 1-siloxybut-3-ynyl side chains, incorporated in the anellation, are easily accessible by the addition of a propargyl metal reagent to a formyl group and silylation of the alcohol. This conveniently allows an anellation at the position of the formyl group under mild conditions. All reactions involve a 2,3-shift of the side chain in the anellation step and thus, provide an easy access to specific substitution patterns. Only in the case of 2-substituted indoles with their highly nucleophilic 3-position a direct hydroarylation without shift is observed. On the other hand, 3-substituted indoles give the same products as 2-substituted indoles. Then, a 3,2-shift in the indole ring system has to be involved. | ||
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| 650 | 4 | |a heterocycles | |
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