A chelation-assisted transformation: synthesis of maleimides by the Rh-catalyzed carbonylation of alkynes with pyridin-2-ylmethylamine.

The Journal of organic chemistry

PubMedID: 17655364

Inoue S, Fukumoto Y, Chatani N. A chelation-assisted transformation: synthesis of maleimides by the Rh-catalyzed carbonylation of alkynes with pyridin-2-ylmethylamine. J Org Chem. 2007;72(17):6588-90.
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.