Chen-Yan, Cai, Si-Jie, Chen, Rohan R., Merchant, Tian, Qin and Kanda, Yuzuru (2024) C3 Selective Hydroxylation of Pyridines via Photochemical Valence Isomerization of Pyridine N-OxidesArticle link copied! Journal of American Chemical Society, 146 (35). pp. 24257-24264.

Abstract

The C–H hydroxylation of the pyridine C3 position is a highly desirable transformation but remains a great challenge due to the inherent electronic properties of this heterocycle core which bring difficulties in chemical reactivity and regioselectivity. Herein we present an efficient method for formal C3 selective hydroxylation of pyridines via photochemical valence isomerization of pyridine N-oxides. This metal-free transformation features operational simplicity and compatibility with a diverse array of functional groups, and the resulting hydroxylated products are amenable to further elaboration to synthetically useful building blocks. The synthetic utility of this strategy is further demonstrated in the effective late-stage functionalization of pyridine-containing medicinally relevant molecules and versatile derivatizations of 3-pyridinols.

Item Type:	Article
Date Deposited:	08 Oct 2024 00:45
Last Modified:	08 Oct 2024 00:45
URI:	https://oak.novartis.com/id/eprint/54032