Palladium-Catalyzed Difunctionalization of Alkenes by Relay Coupling with Propargylic Pyridines: Synthesis of Indolizine and Indolizinone-Containing Bisheterocycles,The Journal of Organic Chemistry

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Palladium-Catalyzed Difunctionalization of Alkenes by Relay Coupling with Propargylic Pyridines: Synthesis of Indolizine and Indolizinone-Containing Bisheterocycles
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-12-03 , DOI: 10.1021/acs.joc.1c02438
Xiao Xiao ₁ , Puren Han ₁ , Huiwen Zhou ₁ , Jianchao Liu ₁

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Palladium-catalyzed arylation/heteroarylation of aryl halide-tethered alkenes with propargylic pyridines has been established, which provides direct and efficient access to various oxindole, azaoxindole, dihydrobenzopyran, indole, and benzofuran-linked indolizines in good yields with a broad substrate scope and high functional group tolerance. This process enables the formation of one C–N and two C–C bonds in a single operation through an intramolecular carbopalladation and cycloisomerization sequence. Furthermore, an indolizinone-linked bisheterocyclic framework containing indole and benzofuran could be synthesized conveniently from tertiary propargylic alcohols involving methyl or phenyl migration.

中文翻译：

通过与炔丙基吡啶的继电器偶联实现烯烃的钯催化双官能化：合成吲哚嗪和含吲哚嗪酮的双杂环

已经建立了钯催化的芳基卤化物连接的烯烃与炔丙基吡啶的芳基化/杂芳基化，可以直接有效地获得各种羟吲哚、氮杂吲哚、二氢苯并吡喃、吲哚和苯并呋喃连接的吲哚腙，收率高，底物范围广，高官能团耐受性。该过程能够通过分子内碳钯化和环异构化序列在一次操作中形成一个 C-N 键和两个 C-C 键。此外，包含吲哚和苯并呋喃的吲哚嗪酮连接的双杂环骨架可以从涉及甲基或苯基迁移的叔炔醇中方便地合成。

更新日期：2021-12-17

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