Ruthenium(II)-Catalyzed Remote C-H Sulfonylation of 2-Pyridones

Fengqi Yang; Pengfei Zhou; Zeng Huang; Junqiu Liao; Guan Huang; Taoyuan Liang; Zhuan Zhang

doi:10.1021/acs.orglett.3c02004

Ruthenium(II)-Catalyzed Remote C-H Sulfonylation of 2-Pyridones

Org Lett. 2023 Aug 11;25(31):5779-5783. doi: 10.1021/acs.orglett.3c02004. Epub 2023 Jul 27.

Authors

Fengqi Yang¹, Pengfei Zhou¹, Zeng Huang¹, Junqiu Liao¹, Guan Huang¹, Taoyuan Liang¹, Zhuan Zhang¹

Affiliation

¹ Guangxi Key Laboratory of Electrochemical Energy Materials, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, P. R. China.

PMID: 37498216
DOI: 10.1021/acs.orglett.3c02004

Abstract

Herein, a ruthenium-mediated remote C-H mono- and disulfonylation of 2-pyridones with arylsulfonyl chlorides is developed. The catalytic system consisting of a [Ru(p-cymene)Cl₂]₂ catalyst and KOAc additive allows 2-pyridones to undergo C3,C5-disulfonylation in 1,4-dioxane, and C5-sulfonylation when the C3-position of 2-pyridones is blocked. The successful transformation of the products and late-stage modification of estrone further highlighted the potential utility and significance of this synthetic protocol. Preliminary mechanistic studies indicated that the remote regioselectivity might be dictated via chelation-assisted ruthenation.