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Updated: Oct 25, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Nickel-Catalyzed Reductive Alkylation of Aldimines with Unactivated Alkyl Iodides
Minji Kim1, Jin Hyun Park1, Won Jun Jang1
1Department of Chemistry and Nanoscience, Ewha Womans University, Seoul, 03760, Republic of Korea.
Abstract:
A nickel-catalyzed reductive alkylation of directing-group-free N-sulfonyl and N-aryl aldimines is reported. The reaction proceeds at ambient temperature and accommodates unactivated primary, secondary, and tertiary alkyl iodides as well as selected activated alkyl bromides with broad functional-group tolerance. Complex molecule-derived alkyl iodides, a gram-scale reaction, and β-amino ester derivatizations demonstrate synthetic utility. Mechanistic studies support nickel-mediated generation of a solution-accessible alkyl radical and are consistent with outer-sphere radical addition to the imine.
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