Preparation of Ketimines from Aryldiazonium Salts, Arenes, and Nitriles via Intermolecular Arylation of N-Arylnitrilium Ions
2018
A transition-metal-free approach for the preparation of N-arylketimines has been developed from the direct reaction of aryldiazonium salts, arenes, and nitriles in a one-pot fashion with the consecutive formation of N–C and C–C bonds. This approach proceeds via an in situ generation of N-arylnitrilium intermediate, which then undergoes intermolecular arylation. This three-component strategy offers a step- and atom-efficient way to N-arylketimines from easily accessible reagents under mild reaction conditions. The characterization of stereochemistry of ketimine was achieved by X-ray crystallographic structure and theoretical calculation. Operational simplicity, shorter reaction time, excellent functional group compatibility, and scalability are the key features of this report.
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