The carbocation-catalyzed intermolecular formal [2 + 2 + 1] cycloaddition of ynamides with quinoxaline N-oxides
Carbocation-catalyzed oxidative [2 + 2 + 1] annulation of two molecules of ynamide with 2,3-dichloroquinoxaline N-oxide enables the facile and convergent assembly of fully substituted symmetric and unsymmetric furan frameworks. The quinoxaline N-oxide presented a remarkable discrepancy to common qui...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
November 4, 2019
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| In: |
ACS catalysis
Year: 2019, Volume: 9, Issue: 12, Pages: 11663-11668 |
| ISSN: | 2155-5435 |
| DOI: | 10.1021/acscatal.9b03911 |
| Online Access: | Resolving-System, Volltext: https://doi.org/10.1021/acscatal.9b03911 Verlag: https://pubs.acs.org/doi/full/10.1021/acscatal.9b03911 
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| Author Notes: | Hongming Jin, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
| Summary: | Carbocation-catalyzed oxidative [2 + 2 + 1] annulation of two molecules of ynamide with 2,3-dichloroquinoxaline N-oxide enables the facile and convergent assembly of fully substituted symmetric and unsymmetric furan frameworks. The quinoxaline N-oxide presented a remarkable discrepancy to common quinoline and pyridine N-oxides. A wide range of functional groups is well compatible due to the mild conditions. The strategy works also for the intramolecular macrocyclization of diynamides for the synthesis of macrocyclic furan derivatives. Moreover, a set of NMR experiments revealed the activation of a triple bond via a carbocation catalyst. |
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| Item Description: | Gesehen am 13.01.2020 |
| Physical Description: | Online Resource |
| ISSN: | 2155-5435 |
| DOI: | 10.1021/acscatal.9b03911 |