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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. 2019

Qiyuan He, and Yusuke Ano, and Naoto Chatani
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. chatani@chem.eng.osaka-u.ac.jp.

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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