钯催化的 7-氮杂吲哚的串联芳基化反应：四芳基 7-氮杂吲哚的聚集诱导发射。
Pd-Catalyzed Sequential Arylation of 7-Azaindoles: Aggregate-Induced Emission of Tetra-Aryl 7-Azaindoles.
机构信息
Special Centre for Molecular Medicine , Jawaharlal Nehru University , New Delhi 110067 , India.
Department of Chemistry , Indian Institute of Technology (Indian School of Mines) , Dhanbad , Jharkhand 826004 , India.
出版信息
J Org Chem. 2019 Nov 1;84(21):14015-14029. doi: 10.1021/acs.joc.9b02187. Epub 2019 Oct 1.
Pd-catalyzed synthesis of multi-aryl 7-azaindoles using sequential arylation of 5-bromo-6-chloro-3-iodo-1-methyl-1-pyrrolo[2,3-] pyridine is established. Four diverse aryl groups are installed in a chemo-selective fashion providing a general method to synthesize sterically encumbered compounds and extended 7-azaindoles in 48-95% yields. Three-selective sequential arylations at C-3, C-5, and C-6 via Suzuki-Miyaura cross-coupling followed by direct C-2 arylation using a Pd catalyst and AgOTf as an additive are highlights of the present work. Interestingly, the tetra-aryl 7-azaindoles showed aggregate-induced emission (AIE) making it potentially useful as fluorophores in OLEDs, sensors, and bio-imaging tools.
Pd 催化的多芳基 7-氮茚的合成，采用 5-溴-6-氯-3-碘-1-甲基-1-吡咯并[2,3-b]吡啶的顺序芳基化反应。以化学选择性方式引入四个不同的芳基基团，提供了一种通用的方法来合成空间位阻化合物和扩展的 7-氮茚，产率为 48-95%。通过Suzuki-Miyaura 交叉偶联在 C-3、C-5 和 C-6 处进行三次选择性顺序芳基化，然后使用 Pd 催化剂和 AgOTf 作为添加剂进行直接 C-2 芳基化，这是本工作的重点。有趣的是，四芳基 7-氮茚表现出聚集诱导发射（AIE），使其有可能作为有机发光二极管（OLED）、传感器和生物成像工具中的荧光团。
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