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Updated: Feb 7, 2026

Gyroid Nickel Nanostructures from Diblock Copolymer Supramolecules
Published on: April 28, 2014
Nickel-Catalyzed Stereospecific C-H Coupling of Benzamides with Epoxides
Shibo Xu1, Kazutaka Takamatsu1, Koji Hirano1
1Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.
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 Csp3 -H functionalization is also achieved in the presence of modified NiCl2 catalysts.
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