Catalytic C–H Functionalization Methods
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Abstract
Abstract
Ligand-controlled chemodivergence in C–H activation remains a significant challenge as multiple reaction pathways exist in the presence of multiple C–H bonds. Here we report a Pd(II)-catalyzed chemodivergent β -methylene C(sp³)–H heteroarylation of free aliphatic acids leading to distinct products enabled by two different classes of bidentate pyridone ligands, respectively. These two ligands also overcome a long-standing inhibitory effect of heteroaryl iodides, demonstrating the potential of this protocol to serve as a general C(sp³)–C(sp 2 ) coupling method using readily available aliphatic acids as the alkylating partner. Mechanistic experiments and DFT analyses reveal that quinoline and the imine motifs of the ligands dictate how the carbon-carbon and carbon-palladium bonds of the key intermediates rotate through π-π interaction and steric control, respectively, decisively splitting the catalytic pathways towards either oxidative or reductive Heck products.
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@article{Hu2026Ligand,
title = {Ligand-Controlled Chemodivergent β-Methylene C(sp3)–H Heteroarylation of Aliphatic Acids},
author = {Liang Hu and Yilin Lu and Xiang‐Lei Han and Jie-Lun Yan and Tao Sheng and TG Murali Dhar and Shuang Liu and Renyu Guo and Shishir Chourey and Jennifer X. Qiao and Jin‐Quan Yu},
journal = {ChemRxiv},
year = {2026},
doi = {10.26434/chemrxiv.15005106/v1},
url = {https://doi.org/10.26434/chemrxiv.15005106/v1}
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