Synthesis of Naphthylpyridines from Unsymmetrical Naphthylheptadiynes and the Configurational Stability of the Biaryl Axis
A series of different unsymmetrically substituted naphthyl-based diynes were synthesized. These substrates formed the foundation for the assembly of novel biaryls containing pyridine moieties with differently substituted five-membered rings in the backbone of the newly formed heterobiaryl system. Th...
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| Main Authors: | , , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
March 21, 2016
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| In: |
The journal of organic chemistry
Year: 2016, Volume: 81, Issue: 8, Pages: 3087-3102 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.5b02190 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.5b02190
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| Author Notes: | Fabian Fischer, Alexander F. Siegle, Marek Checinski, Christine Fischer, Karolin Kral, Richard Thede, Oliver Trapp, Marko Hapke |
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| 245 | 1 | 0 | |a Synthesis of Naphthylpyridines from Unsymmetrical Naphthylheptadiynes and the Configurational Stability of the Biaryl Axis |c Fabian Fischer, Alexander F. Siegle, Marek Checinski, Christine Fischer, Karolin Kral, Richard Thede, Oliver Trapp, Marko Hapke |
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| 520 | |a A series of different unsymmetrically substituted naphthyl-based diynes were synthesized. These substrates formed the foundation for the assembly of novel biaryls containing pyridine moieties with differently substituted five-membered rings in the backbone of the newly formed heterobiaryl system. The key step for their efficient construction was the photo- and cobalt-catalyzed [2 + 2 + 2] cycloaddition reaction between the corresponding naphthyldiyne and aceto- or benzonitrile. The heterobiaryl products have been isolated and investigated with respect to the configurational stability of their biaryl axis using dynamic chiral HPLC; subtle effects of the substitution pattern on the stability of the axis were observed. For several compounds the activation barriers (ΔG‡) of racemization were determined. Suitable substitution of the five-membered ring backbone exemplarily allowed the Co-catalyzed enantioselective cyclization to yield the enantiomerically enriched heterobiaryl. | ||
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| 700 | 1 | |a Checinski, Marek |e VerfasserIn |4 aut | |
| 700 | 1 | |a Fischer, Christine |e VerfasserIn |4 aut | |
| 700 | 1 | |a Kral, Karolin |e VerfasserIn |4 aut | |
| 700 | 1 | |a Thede, Richard |e VerfasserIn |4 aut | |
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