Synthesis of aryl and heteroaryl tetrafluoro-λ6-sulfanyl chlorides from diaryl disulfides using trichloroisocyanuric acid and potassium fluoride

Ibrayim Saidalimu; Yumeng Liang; Kiyoteru Niina; Kazuhiro Tanagawa; Norimichi Saito; Norio Shibata

doi:10.1039/C9QO00191C

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Synthesis of aryl and heteroaryl tetrafluoro-λ⁶-sulfanyl chlorides from diaryl disulfides using trichloroisocyanuric acid and potassium fluoride†

Ibrayim Saidalimu,^a Yumeng Liang,^a Kiyoteru Niina,^a Kazuhiro Tanagawa,^a Norimichi Saito^b and Norio Shibata

*^ac

Author affiliations

* Corresponding authors

^a Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
E-mail: nozshiba@nitech.ac.jp

^b Pharmaceutical Division, Ube Industries, Ltd, Seavans North Bldg, 1-2-1 Shibaura, Minato-ku, Tokyo 105-8449, Japan

^c Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, 321004 Jinhua, China

Abstract

We present a catalyst-free method for the synthesis of aryl and heteroaryl tetrafluoro-λ⁶-sulfanyl chlorides (Ar-SF₄Cl) by using trichloroisocyanuric acid and potassium fluoride in acetonitrile. The method has wide substrate generality and proceeded well with high yields even in the absence of acid catalysts. The preparation of meta- and para-SF₄Cl-substituted pyridines using TCCA was achieved for the first time.

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Article information

DOI: https://doi.org/10.1039/C9QO00191C
Article type: Research Article
Submitted: 02 Feb 2019
Accepted: 21 Feb 2019
First published: 22 Feb 2019

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Org. Chem. Front., 2019,6, 1157-1161

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Synthesis of aryl and heteroaryl tetrafluoro-λ⁶-sulfanyl chlorides from diaryl disulfides using trichloroisocyanuric acid and potassium fluoride

I. Saidalimu, Y. Liang, K. Niina, K. Tanagawa, N. Saito and N. Shibata, Org. Chem. Front., 2019, 6, 1157 DOI: 10.1039/C9QO00191C

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