Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles
An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction pro...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
6 February 2021
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| In: |
Tetrahedron
Year: 2021, Volume: 83, Pages: 1-16 |
| ISSN: | 1464-5416 |
| DOI: | 10.1016/j.tet.2021.131985 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1016/j.tet.2021.131985 Verlag, lizenzpflichtig, Volltext: https://www.sciencedirect.com/science/article/pii/S0040402021000843 
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| Author Notes: | Robert H.E. Schirmacher, Daniel Rösch, Franziska Thomas |
| Summary: | An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles. |
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| Item Description: | Gesehen am 04.08.2021 |
| Physical Description: | Online Resource |
| ISSN: | 1464-5416 |
| DOI: | 10.1016/j.tet.2021.131985 |