Pd-Catalyzed Formal [3+3] Annulation of Benzylic gem-Diacetates: Synthesis of Various (Hetero)Arene-Fused Benzo[f]chromenes
Unlike that of benzyl acetates, the chemistry of benzyl gem-diacetates is rarely explored under metal catalysis. Here, we describe the first palladium-catalyzed cascade annulative allylic alkylation of benzylic gem-diacetates to access complex analogues of (hetero)arene-fused benzo[f]chromenes, w...
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| Published in: | Organometallics Vol. 42; no. 18; pp. 2460 - 2466 |
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| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
American Chemical Society
25-09-2023
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| Online Access: | Get full text |
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| Summary: | Unlike that of benzyl acetates, the chemistry of benzyl gem-diacetates is rarely explored under metal catalysis. Here, we describe the first palladium-catalyzed cascade annulative allylic alkylation of benzylic gem-diacetates to access complex analogues of (hetero)arene-fused benzo[f]chromenes, which find relevance in medicinal chemistry and materials science. This synthetic feat has been achieved through the formal [3+3] heterocyclization of easily accessible (hetero)aryl gem-diacetates and readily available 2-naphthols under neutral conditions. Detailed mechanistic studies and synthetic elaborations have also been performed. |
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| ISSN: | 0276-7333 1520-6041 |
| DOI: | 10.1021/acs.organomet.2c00472 |