Organic Letters
Organic Letters
5 years ago

Ni-Catalyzed Reductive Cross-Coupling of Amides with Aryl Iodide Electrophiles via C–N Bond Activation

Ni-Catalyzed Reductive Cross-Coupling of Amides with Aryl Iodide Electrophiles via C–N Bond Activation
Wenzhong Zhang, Shengyang Ni, Jianlin Han, Haibo Mei, Yi Pan
A Ni-catalyzed reductive cross-coupling reaction between two electrophiles, amides and aryl iodides, has been developed. This work is the first example using amide as an electrophile to couple with another electrophile, instead of using highly basic and pyrophoric nucleophiles. Furthermore, the Ni catalyst chemoselectively inserting the C–N bond of amide triggered the reductive cross-coupling reaction, which solves the problem that the Ni catalyst preferentially inserts the more reactive C–I bond to form a self-coupling product.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00831

DOI: 10.1021/acs.orglett.7b00831

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