Directing Group Enables Electrochemical Selectively <i>Meta</i>-Bromination of Pyridines under Mild Conditions
Yanwei Wu, Shanghui Xu, Hong Wang, Dongxu Shao, Qiqi Qi, Yi Lu, Li Ma, Jianhua Zhou, Wei Hu, Wei Gao, Jianbin Chen
Abstract
Without the use of catalysts and oxidants, a facile and sustainable electrochemical bromination protocol was developed. By introducing the directing groups, the regioselectivity of pyridine derivatives could be controlled at the meta-position utilizing the inexpensive and safe bromine salts at room temperature. A variety of brominated pyridine derivatives were obtained in 28–95% yields, and the reaction could be readily performed at a gram scale. By combining the installation and removing the directing group, the concept of meta-bromination of pyridines could be verified.
Topics & Concepts
HalogenationBromineRegioselectivityPyridineChemistryElectrochemistryCatalysisGroup (periodic table)Combinatorial chemistryOrganic chemistryElectrodePhysical chemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsVanadium and Halogenation Chemistry