Copper-assisted preparation of pyridinyl sulfonate esters from hydroxypyridines and sodium sulfinates

Qian Li; Haibo Zhu; Yishuai Liu; Liu Yang; Qiangwen Fan; Zongbo Xie; Zhang-Gao Le

doi:10.1039/d1ra08568a

Copper-assisted preparation of pyridinyl sulfonate esters from hydroxypyridines and sodium sulfinates

RSC Adv. 2022 Jan 20;12(5):2736-2740. doi: 10.1039/d1ra08568a. eCollection 2022 Jan 18.

Authors

Qian Li¹, Haibo Zhu^{1

2}, Yishuai Liu¹, Liu Yang¹, Qiangwen Fan^{1

3}, Zongbo Xie¹, Zhang-Gao Le¹

Affiliations

¹ Jiangxi Province Key Laboratory of Synthetic Chemistry, School of Chemistry, Biology and Material Science, East China University of Technology 330013 Nanchang China hbzhu@ecut.edu.cn fanqw2019@ecut.edu.cn zbxie@ecut.edu.cn.
² Jiangxi Province Key Laboratory of Polymer Micro/Nano Manufacturing and Devices, East China University of Technology Nanchang 330013 China.
³ Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation, East China University of Technology Nanchang 330013 China.

Abstract

An efficient and powerful copper-assisted method for the effective conversion of a broad range of hydroxypyridines and sodium sulfinates into their corresponding pyridinyl tosylates was developed. Key features of this base- and ligand-free protocol include using the cheap and readily available CuBr₂ as a medium and the use of sodium sulfinates as formal sulfonylation reagents. A variety of functional pyridinyl tosylates could be formed with good yields, which can easily be converted into C-C and C-N bond-containing compounds.