Chemoselectivity control: gold(I)-catalyzed synthesis of 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans from 1-(alkynyl)-7-oxabicyclo[4.1.0]heptan-2-ones
New and chemoselective gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]- heptan-2-ones were developed. Two completely different products—6,7-dihydrobenzofuran-4(5H)-ones and benzofurans—could be obtained from the same starting material. The selectivity is determined by the li...
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| Hauptverfasser: | , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
July 23, 2013
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| In: |
Chemistry - a European journal
Year: 2013, Jahrgang: 19, Heft: 37, Pages: 12512-12516 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201301698 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201301698 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201301698 
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| Verfasserangaben: | Tao Wang, Shuai Shi, Mie Højer Vilhelmsen, Tuo Zhang, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
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| 520 | |a New and chemoselective gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]- heptan-2-ones were developed. Two completely different products—6,7-dihydrobenzofuran-4(5H)-ones and benzofurans—could be obtained from the same starting material. The selectivity is determined by the ligand of the gold catalyst: triphenylphosphine delivers 6,7-dihydrobenzofuran-4(5H)-ones, and 1,3-bis(diisopropylphenyl)imidazol-2-ylidene leads to benzofurans. Eleven examples of each case are provided. The mechanistic suggestions for the pathways to both product types are supported by isotope labeling experiments. | ||
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