Final Thoughts on Chemistry for 1-(2-Hydroxyethyl)-1H-pyrrole-2,5-dione

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The Pd-catalyzed C-H alkylation of ortho -methyl-substituted aromatic amides with maleimide occurs preferentially at the ortho -methyl C-H bond over the ortho -C-H bond

The reaction of ortho-methyl-substituted aromatic amides with maleimides in the presence of Pd(OAc)2 and AgOAc results in C-H alkylation at the ortho-methyl C-H bond. DFT calculations indicate that the formation of a five-membered palladacycle is a kinetically favorable step, but the insertion of the maleimide into the six-membered palladacycle is energetically favored.

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Reference£º
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem