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Nickel‐Catalyzed Stereospecific C−H Coupling of Benzamides with Epoxides
Author(s) -
Xu Shibo,
Takamatsu Kazutaka,
Hirano Koji,
Miura Masahiro
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807664
Subject(s) - stereospecificity , catalysis , chemistry , nickel , palladium , surface modification , coupling (piping) , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
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 NiCl 2 catalysts.