H-phosphonate-mediated sulfonylation of heteroaromatic N-oxides: a mild and metal-free one-pot synthesis of 2-sulfonyl quinolines/pyridines

Kai Sun; Xiao-Lan Chen; Xu Li; Ling-Bo Qu; Wen-Zhu Bi; Xi Chen; Hui-Li Ma; Song-Tao Zhang; Bo-Wen Han; Yu-Fen Zhao; Chao-Jun Li

doi:10.1039/C5CC04484G

H-phosphonate-mediated sulfonylation of heteroaromatic N-oxides: a mild and metal-free one-pot synthesis of 2-sulfonyl quinolines/pyridines†

Kai Sun,^a Xiao-Lan Chen,*^a Xu Li,^a Ling-Bo Qu,*^ab Wen-Zhu Bi,^a Xi Chen,^a Hui-Li Ma,^a Song-Tao Zhang,^a Bo-Wen Han,^a Yu-Fen Zhao*^ac and Chao-Jun Li^d

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* Corresponding authors

^a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, China
E-mail: chenxl@zzu.edu.cn
Fax: +86 371 67767051
Tel: +86 371 67767051

^b Chemistry and Chemical Engineering School, Henan University of Technology, Zhengzhou, China

^c Department of Chemistry, Xiamen University, Xiamen, China

^d Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, Montreal, Quebec H3A0B8, Canada

Abstract

A smart H-phosphonate-mediated synthetic strategy for the sulfonylation of heteroaromatic N-oxides has been developed, by which a large variety of 2-sulfonyl quinolines/pyridines were synthesized starting from easily available sulfonyl chlorides, diisopropyl H-phosphonate and pyridine/quinoline N-oxides in one pot under metal-free conditions at room temperature.

Chemical Communications

H-phosphonate-mediated sulfonylation of heteroaromatic N-oxides: a mild and metal-free one-pot synthesis of 2-sulfonyl quinolines/pyridines†

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H-phosphonate-mediated sulfonylation of heteroaromatic N-oxides: a mild and metal-free one-pot synthesis of 2-sulfonyl quinolines/pyridines

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