Iridium‐Catalyzed Intramolecular Methoxy C−H Addition to Carbon–Carbon Triple Bonds: Direct Synthesis of 3‐Substituted Benzofurans from o‐Methoxyphenylalkynes |
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| Authors: | Takeru Torigoe Dr Toshimichi Ohmura Prof Michinori Suginome |
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| Institution: | Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, Japan |
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| Abstract: | Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C?H bond of a methoxy group in 1‐methoxy‐2‐(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p‐xylene at 135 °C in the presence of an iridium catalyst. The initial 5‐exo cyclization products underwent double‐bond migration during the reaction to give 3‐(arylmethyl)benzofurans in high yields. |
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| Keywords: | C− C bond formation C− H activation hydroalkylation iridium oxygen heterocycles |
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