Synthesis of Oxygenated ortho -Methylbenzaldehydes via Aryne [2+2] Cycloaddition and Benzocyclobutenol Ring Opening
Herein, a two-step procedure for the preparation of oxygenated -methylbenzaldehyde derivatives, starting from commercially available bromoarenes, is described. The synthesis features the simultaneous and highly regioselective installation of both the methyl and the formyl group onto the benzene core...
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Veröffentlicht in: | Chimia 2018-12, Vol.72 (12), p.870-873 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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Zusammenfassung: | Herein, a two-step procedure for the preparation of oxygenated
-methylbenzaldehyde derivatives, starting from commercially available bromoarenes, is described. The synthesis features the simultaneous and highly regioselective installation of both the methyl and the formyl group onto the benzene core
benzyne [2+2] cycloadditions with acetaldehyde lithium enolate to give the corresponding benzocyclobutenols in high yields. Bond-selective ring opening of the benzocyclobutenols under basic conditions in methanol delivers the title compounds. |
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ISSN: | 0009-4293 2673-2424 |
DOI: | 10.2533/chimia.2018.870 |