C–H activation and functionalization is a research field of active and growing interest in organic synthesis. Collaboration between experimental and computational researchers has led to advances in understandings and innovative new methods. We have studied the mechanisms of Pd(II)-catalyzed C-H olefinations of toluene derivatives that employ a nitrile-containing template. The Pd-Ag heterodimer in determining the meta-chemoselectivity has been discovered. Jin-Quan Yu’s group recently reported the discovery of chiral acetyl-protected aminoethyl quinoline ligands (APAQ) that enable asymmetric palladium insertion into prochiral C–H bonds on a single methylene carbon center. Through computational studies, we developed the model that explains the stereochemistry of this reaction. In addition, the origins of the dramatic differences between 6-membered and 5-membered chelation in the b-methylene C(sp3)–H activation reactions by Pd(II) catalyst were explained with a variety of density functional theory calculations.

Computational exploration of Pd(II)-catalyzed C-H activation and functionalization

254th National Meeting (2017)

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