Visible-light-induced meta-selective sulfonylation of pyridine via an EDA complex DOI

Yong-Qing Ye,

Zhipeng Ye,

Meng Guo

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Pyridine is a versatile structural unit found in broad spectrum of pharmaceuticals, agrochemicals, and materials. Achieving selective meta-functionalization under mild conditions remains challenging due to its inherent electronic properties. In this work, we accomplished photoinduced method for meta-selective sulfonylation pyridines, facilitated by an electron donor-acceptor (EDA) complex between iodide ions sulfonyl chlorides. The reaction proceeds via oxazino-pyridine intermediate, with chloride acting as the radical precursor. This protocol stands out mild, photocatalyst-free conditions, high C5-selectivity, good scalability, offering promising approach synthesis meta-sulfonylated pyridines.

Language: Английский

Formal meta-C–H-Fluorination of Pyridines and Isoquinolines through Dearomatized Oxazinopyridine Intermediates DOI
Malte Haring, Kuruva Balanna, Qiang Cheng

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(45), P. 30758 - 30763

Published: Nov. 1, 2024

Organofluorine compounds, including fluorinated pyridines and isoquinolines, play a crucial role in pharmaceuticals, agrochemicals, materials science. However, step-economic selective C-H-functionalization to access these azaarenes is still underexplored, with

Language: Английский

Citations

5
Unlocking redox-active reactivity of dearomatized pyridines with photochemistry toward meta-C–H functionalization of pyridines DOI

Mingkai Yang,

Mei Wang,

Haiman Zhang

et al.

Chem Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 101326 - 101326

Published: March 1, 2025

Language: Английский

Citations

0
ANROFRC Enables Skeletal Editing of 4-Arylpyrimidines into Diverse Nitrogen Heteroaromatics DOI Creative Commons
Haiyan Fu, Shun Li,

Yonglin Shi

et al.

Research Square (Research Square), Journal Year: 2025, Volume and Issue: unknown

Published: March 25, 2025

Abstract Scaffold hopping is a key strategy in drug discovery. While one-to-one scaffold strategies are thriving and evolving, one-to-multiple remain challenging to design. We present here novel for the skeletal editing of pyrimidines into wide range heteroarenes through addition nucleophiles, ring-opening, fragmentation, ring-closing (ANROFRC) processes. This method features in situ generation vinamidinium salt intermediate, which serves as unique N-C-C-C four-atom (A4) synthon that reacts with A1 A2 synthons. Mechanistic studies reveal C4-aryl substituents play crucial role stabilizing intermediate. work provides powerful tool systematic construction modification nitrogen heterocycles, thereby expanding conventional molecular techniques.

Language: Английский

Citations

0
Visible-light-induced meta-selective sulfonylation of pyridine via an EDA complex DOI

Yong-Qing Ye,

Zhipeng Ye,

Meng Guo

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Pyridine is a versatile structural unit found in broad spectrum of pharmaceuticals, agrochemicals, and materials. Achieving selective meta-functionalization under mild conditions remains challenging due to its inherent electronic properties. In this work, we accomplished photoinduced method for meta-selective sulfonylation pyridines, facilitated by an electron donor-acceptor (EDA) complex between iodide ions sulfonyl chlorides. The reaction proceeds via oxazino-pyridine intermediate, with chloride acting as the radical precursor. This protocol stands out mild, photocatalyst-free conditions, high C5-selectivity, good scalability, offering promising approach synthesis meta-sulfonylated pyridines.

Language: Английский

Citations

0