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Synthesis 2018; 50(12): 2407-2415
DOI: 10.1055/s-0036-1591559
paper
© Georg Thieme Verlag Stuttgart · New York

Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts

Jun Dong
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: jxxu@mail.buct.edu.cn
,
Jiaxi Xu*
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: jxxu@mail.buct.edu.cn
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (Nos. 21572017 and 21772010).
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Publication History

Received: 22 January 2018

Accepted after revision: 05 March 2018

Publication Date:
04 April 2018 (online)

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Abstract

A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert-butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.

Key words

benzynes - diaryliodonium salts - sulfides - sulfones - thiiranes - ring opening

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591559. Copies of the 1H and 13C NMR spectra of products 4 are included.
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