A Chelation-Assisted Transformation:  Synthesis of Maleimides by the Rh-Catalyzed Carbonylation of Alkynes with Pyridin-2-ylmethylamine

The reaction of alkynes 1 with CO and pyridin-2-ylmethylamine (2) in the presence of Rh4(CO)12/P(OEt)3 results in the incorporation of two molecules of CO leading to maleimide derivatives 3. The coordination of the pyridine nitrogen in 2 to a rhodium center is essential for the reaction to proceed.