“Golden” cascade cyclization to Benzo[c]-Phenanthridines
Herein, we describe a gold-catalyzed cascade cyclization of Boc-protected benzylamines bearing two tethered alkyne moieties in a domino reaction initiated by a 6-endo-dig cyclization. The reaction was screened intensively, and the scope was explored, resulting in nine new Boc-protected dihydrobenzo[...
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| Main Authors: | , , , , , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
September 12, 2021
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| In: |
Chemistry - a European journal
Year: 2021, Volume: 27, Issue: 59, Pages: 14778-14784 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202102134 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202102134 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202102134 
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| Author Notes: | Christoph M. Hendrich, Sebastian Senn, Lea Haas, Marvin T. Hoffmann, Ute Zschieschang, Luca C. Greiner, Frank Rominger, Matthias Rudolph, Hagen Klauk, Andreas Dreuw, and A. Stephen K. Hashmi |
| Summary: | Herein, we describe a gold-catalyzed cascade cyclization of Boc-protected benzylamines bearing two tethered alkyne moieties in a domino reaction initiated by a 6-endo-dig cyclization. The reaction was screened intensively, and the scope was explored, resulting in nine new Boc-protected dihydrobenzo[c]phenanthridines with yields of up to 98 %; even a π-extension and two bidirectional approaches were successful. Furthermore, thermal cleavage of the Boc group and subsequent oxidation gave substituted benzo[c]phenanthridines in up to quantitative yields. Two bidirectional approaches under the optimized conditions were successful, and the resulting π-extended molecules were tested as organic semiconductors in organic thin-film transistors. |
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| Item Description: | Gesehen am 28.03.2023 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202102134 |