Directing Group Enables Electrochemical Selectively Meta-Bromination of Pyridines under Mild Conditions

J Org Chem. 2021 Nov 19;86(22):16144-16150. doi: 10.1021/acs.joc.1c00923. Epub 2021 Jun 15.

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.