Gold-catalyzed regio- and stereoselective α-acyloxy-β-alkynylation of ynol ethers
Enol esters and conjugated enynes are valuable structural motifs for synthetic chemistry and material sciences. Herein, the synthesis of tetra-substituted enol ester 2-iodobenzoate derivatives was achieved in good yields at room temperature through a gold-catalyzed acyloxyalkynylation of sensitive y...
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| Hauptverfasser: | , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
17 February 2023
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| In: |
The journal of organic chemistry
Year: 2023, Jahrgang: 88, Heft: 5, Pages: 2908-2920 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.2c02597 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.2c02597
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| Verfasserangaben: | Yaowen Liu, Chunyu Han, Hongwei Shi, Alexandra V. Mackenroth, Linghua Zhang, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
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| 245 | 1 | 0 | |a Gold-catalyzed regio- and stereoselective α-acyloxy-β-alkynylation of ynol ethers |c Yaowen Liu, Chunyu Han, Hongwei Shi, Alexandra V. Mackenroth, Linghua Zhang, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
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| 520 | |a Enol esters and conjugated enynes are valuable structural motifs for synthetic chemistry and material sciences. Herein, the synthesis of tetra-substituted enol ester 2-iodobenzoate derivatives was achieved in good yields at room temperature through a gold-catalyzed acyloxyalkynylation of sensitive ynol ethers with ethynylbenziodoxolones (EBXs), the latter acting as bifunctional reactants. The conversion is highly regioselective with a broad substrate scope. Mechanistically, an Au(III) species is the key intermediate of an Au(I)/Au(III) redox cycle. The reaction is synthetically useful and can easily be scaled up to gram scale. | ||
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