Synthesis of masked haloareneboronic acids via iridium-catalyzed aromatic C-H borylation with 1,8-naphthalenediaminatoborane (danBH) |
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Authors: | Noriyuki Iwadate |
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Institution: | Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 606-8501, Japan |
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Abstract: | “Masked” areneboronic acids have been prepared by Ir-catalyzed C-H borylation of arenes. A Ir(OMe)(cod)]2 complex with a DPPE ligand showed the highest catalytic activity in the C-H borylation of benzene at 80 °C. The reaction system can be applied to substituted arenes, including halogen-substituted arenes. 1,3-Dihalobenzenes undergo the C-H borylation at their 5-positions in a regioselective fashion, affording 3,5-dihaloareneboronic acid derivatives, which serve as useful coupling modules for the convergent dendrimer synthesis. |
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Keywords: | C-H borylation Iridium catalysis Cross-coupling Iterative synthesis Dendrimer synthesis |
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