Nickel‐Catalyzed Stereospecific C−H Coupling of Benzamides with Epoxides |
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| Authors: | Shibo Xu Kazutaka Takamatsu Prof Dr Koji Hirano Prof Dr Masahiro Miura |
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| Affiliation: | Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka, Japan |
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| Abstract: | A Ni(OAc)2‐catalyzed C?H coupling of 8‐aminoquinoline‐derived benzamides with epoxides has been developed. The reaction proceeds with concomitant removal of the 8‐aminoquinoline auxiliary to form the corresponding 3,4‐dihydroisocoumarins directly. Additionally, the nickel catalysis is stereospecific, and the cis‐ and trans‐epoxides are converted into the corresponding cis‐ and trans‐dihydroisocoumarins with retention of configuration, which is complementary to previously reported palladium catalysis. Moreover, while still preliminary, the C ?H functionalization is also achieved in the presence of modified NiCl2 catalysts. |
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| Keywords: | C− H coupling epoxides lactones nickel stereospecificity |
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