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Updated: Mar 15, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
N-H Imine as a Powerful Directing Group for Cobalt-Catalyzed Olefin Hydroarylation
Wengang Xu1, Naohiko Yoshikai2
1Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
Abstract:
N-alkyl and N-aryl imines have been frequently used as directing groups in rhodium- and cobalt-catalyzed hydroarylation reactions of olefins and alkynes. However, the scope of such hydroarylation reactions has been limited by the difficulty of preparation of sterically hindered imines by condensation, and also by the steric bulkiness of the imine group itself. Reported herein is that an N-H imine serves as an alternative and highly effective directing group for cobalt-catalyzed hydroarylation of olefins, and unlocks many of the limitations associated with the previously employed N-aryl imine directing group. The power of this minimal nitrogen directing group is manifested in a fourfold ortho alkylation of benzophenone imine, and it occurs rapidly at ambient temperature.
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