Palladium‐Catalyzed Intermolecular Acylation of Aryl Diazoesters with ortho‐Bromobenzaldehydes |
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| Authors: | Yinghua Yu Dr. Qianqian Lu Prof. Dr. Gui Chen Prof. Dr. Chunsen Li Prof. Dr. Xueliang Huang |
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| Affiliation: | 1. http://www.fjirsm.cas.cn/huangxl/;2. Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fujian, China;3. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fujian, China |
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| Abstract: | In this work, we describe a palladium‐catalyzed intermolecular O acylation of α‐diazoesters with ortho‐bromobenzaldehydes. The C(sp2)?H bond activation of the aldehyde is enabled by migratory insertion of a palladium carbene intermediate. The diazoesters act as modular three‐atom units to build up key seven‐membered palladacycles, which are transformed into a variety of isocoumarin derivatives upon reductive elimination. Mechanistic experiments and DFT calculations provide insight into the reaction pathway. |
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| Keywords: | acylation carbene complexes metallacycles ortho-bromobenzaldehydes palladium |
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