Copper-free Sandmeyer-type Reaction for the Synthesis of Sulfonyl Fluorides

Tao Zhong, Meng-Ke Pang, Zhi-Da Chen, Bin Zhang, Jiang Weng* and Gui Lu

*School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, P. R. China, Email: wengj2mail.sysu.edu.cn

T. Zhong, M.-K. Pang, Z.-D. Chen, B. Zhang, J. Weng, G. Lu, Org. Lett., 2020, 22, 2941-2945.

DOI: 10.1021/acs.orglett.0c00823

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Abstract

In a copper-free Sandmeyer-type fluorosulfonylation reaction with Na₂S₂O₅ as the sulfur dioxide source and Selectfluor as fluorine source, aryldiazonium salts are transformed into sulfonyl fluorides. In situ diazotization enables the use of aromatic amines as substrates. The method offers broad functional group tolerance, gram-scale synthesis and late-stage fluorosulfonylation.

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Key Words

Sandmeyer Reaction, Sulfonyl Fluorides, Sodium Peroxydisulfate, Selectfluor

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ID: J54-Y2020