In 2022,Liu, Zhong; He, Jia-Hao; Zhang, Ming; Shi, Zhu-Jun; Tang, Han; Zhou, Xin-Yue; Tian, Jun-Jie; Wang, Xiao-Chen published an article in Journal of the American Chemical Society. The title of the article was 《Borane-Catalyzed C3-Alkylation of Pyridines with Imines, Aldehydes, or Ketones as Electrophiles》.COA of Formula: C5H6BNO2 The author mentioned the following in the article:
Achieving C3-selective pyridine functionalization is a longstanding challenge in organic chem. The existing methods, including electrophilic aromatic substitution and C-H activation, often require harsh reaction conditions and excess pyridine and generate multiple regioisomers. Herein, authors report a method for borane-catalyzed tandem reactions that result in exclusively C3-selective alkylation of pyridines. These tandem reactions consist of pyridine hydroboration, nucleophilic addition of the resulting dihydropyridine to an imine, an aldehyde, or a ketone, and subsequent oxidative aromatization. Because the pyridine is the limiting reactant and the reaction conditions are mild, this method constitutes a practical tool for late-stage functionalization of structurally complex pharmaceuticals bearing a pyridine moiety. In the experimental materials used by the author, we found Pyridin-3-ylboronic acid(cas: 1692-25-7COA of Formula: C5H6BNO2)
Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. Pyridine’s structure is isoelectronic with that of benzene, but its properties are quite different. Pyridine is completely miscible with water, whereas benzene is only slightly soluble. Like all hydrocarbons, benzene is neutral (in the acid–base sense), but because of its nitrogen atom, pyridine is a weak base.COA of Formula: C5H6BNO2