1266570-07-3

Upstream product

• 93-98-1 N-phenyl benzoyl amide 
• 2132-62-9 4,4'-dimethoxydiphenylacetylene 
• 140437-02-1 2-phenoxy-N-phenylbenzamide 

Relevant academic research and scientific papers

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 ofortho-phenoxy-substituted aromatic amides with alkynes in the presence of LiOtBu 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 °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.

Pd/C-catalyzed synthesis of N-aryl and N-alkyl isoquinolones via C[sbnd]H/N[sbnd]H activation

Pd/C-catalyzed direct synthesis of N-aryl and N-alkyl isoquinolones was developed via the annulation reactions of benzamides and alkynes in high yields (up to 99%) through the cleavage of C[sbnd]H/N[sbnd]H bonds. The reaction was ligand-free and air was used as oxidant. High regioselectivities were found when unsymmetrical alkynes or meta-benzamides were used as substrates. The heterocyclic carboxamide substrates, such as furan and thiophene derivatives, also afforded the corresponding products in high yields.

Rhodium-catalyzed oxidative coupling/cyclization of benzamides with alkynes via C-H bond cleavage

Oxidative coupling of primary, secondary, and tertiary benzamides with internal alkynes proceeds efficiently under rhodium catalysis to selectively give the corresponding 1:1 and 1:2 coupling products, accompanied by C-H and/or N-H bond cleavages. Some of the products exhibit intense fluorescence in the solid state.