Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp3–sp3 Coupling
A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and decarboxylation under mild reaction conditions, a proc...
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| Veröffentlicht in: | Journal of organic chemistry 2022-06, Vol.87 (11), p.7557-7564 |
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| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and decarboxylation under mild reaction conditions, a process facilitated by the formation of a stabilized aromatic anion. The regioselective allylic coupling of this intermediate afforded a variety of functionalized phthalides in 73–96% yields. |
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| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/acs.joc.2c00723 |