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Pd-Catalyzed Formal [3+3] Annulation of Benzylic gem-Diacetates: Synthesis of Various (Hetero)Arene-Fused Benzo[f]chromenes

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ORGANOMETALLICS
卷 42, 期 18, 页码 2460-2466

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AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.2c00472

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  1. SERB [DST/SJF/CSA-01/2017-18]
  2. IISER Mohali

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In this study, we described the first palladium-catalyzed cascade annulative allylic alkylation of benzylic gem-diacetates to access complex analogues of (hetero)arene-fused benzo[f]chromenes, which have relevance in medicinal chemistry and materials science.
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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