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Palladium-Catalyzed Dearomative Heck/Suzuki Coupling of C2-Deuterated or C2-Nonsubstituted Indoles
Organic Letters ( IF 5.2 ) Pub Date : 2024-03-15 , DOI: 10.1021/acs.orglett.4c00166
Wei-Yang Gao 1 , Gao-Yang Yu 1 , Yan-Yu Li 2 , Ren-Xiao Liang 1 , Xin Hong 2 , Yi-Xia Jia 1, 3
Affiliation  

A palladium-catalyzed dearomative diarylation of C2-deuterated or C2-nonsubstituted indoles through domino Heck/Suzuki coupling is established. Relying on electron-deficient phosphite ligand, side reactions including intermolecular Suzuki coupling and intramolecular C–D/H arylation are inhibited and a wide range of 2,3-diarylated indolines bearing vicinal tertiary stereocenters including deuterated ones are afforded in moderate to excellent yields (up to 94%) and excellent diastereoselectivities (>20:1). The catalyst loading can be lowered to 0.02 mol % at elevated temperature.

中文翻译:

钯催化 C2-氘代或 C2-未取代吲哚的脱芳香 Heck/Suzuki 偶联

建立了通过多米诺赫克/铃木偶联进行的钯催化的 C2-氘代或 C2-未取代吲哚的脱芳香二芳基化反应。依靠缺电子亚磷酸酯配体,包括分子间 Suzuki 偶联和分子内 C-D/H 芳基化在内的副反应受到抑制,并且以中等至优异的产率提供了各种带有邻位三级立体中心(包括氘代立体中心)的 2,3-二芳基化二氢吲哚(高达 94%)和出色的非对映选择性(>20:1)。在高温下催化剂负载量可降低至 0.02 mol%。
更新日期:2024-03-15
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