Nickel-catalyzed C-O/N-H, C-S/N-H, and C-CN/N-H annulation of aromatic amides with alkynes: C-O, C-S, and C-CN activation

The Ni-catalyzed reaction of ortho-phenoxy-substituted aromatic amides with alkynes in the presence of (LiOBu)-Bu-t as a base results in C-O/N-H annulation with the formation of 1(2H)-isoquinolinones. The use of a base is essential for the reaction to proceed. The reaction proceeds, even in the absence of a ligand, and under mild reaction conditions (40 degrees C). An electron-donating group on the aromatic ring facilitates the reaction. The reaction was also applicable to carbamate (C-O bond activation), methylthio (C-S bond activation), and cyano (C-CN bond activation) groups as leaving groups.

Automated summary

The Ni-catalyzed reaction involves annulation of ortho-phenoxy-substituted aromatic amides with alkynes to form 1(2H)-isoquinolinones in the presence of (LiOBu)-Bu-t as a base. The reaction proceeds even without a ligand under mild conditions at 40 degrees C. An electron-donating group on the aromatic ring facilitates the reaction, which is also applicable to various leaving groups such as carbamate, methylthio, and cyano.