Huang Group
School of Chemical Biology & Biotechnology

Huan Sun, Yi Zhang and Ping Chen’s work has been published in Adv. Synth. Catal.! Congratulations!


Ligand-Assisted Palladium(II)/(IV) Oxidation for sp3 C-H Fluorination

Huan Sun, Yi Zhang, Ping Chen, Yun-Dong Wu*, Xinhao Zhang*, and Yong Huang*,  Adv. Synth. Catal. 2016, 358, 1946(Very Important Paper, Front Cover

The direct functionalization of inert sp3 C-H bonds is limited to a few bond types. Although the activation of sp3 C-H bonds can be accomplished under mild conditions using palladium catalysts, the subsequent functionalization is not trivial due to the high energy required to convert palladium(II) to palladium(IV). We have systematically studied the palladium oxidation using computation-guided experiments for reactions involving strong chelation control. We find that a mild external ligand could significantly accelerate the oxidation of palladium(II) to palladium(IV) for strong bidentate directing groups.The acceleration is believed to be a result of ligand stabilization of both the palladium(II) and palladium(IV) intermediates.