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Synthesis 2018; 50(12): 2407-2415
DOI: 10.1055/s-0036-1591559
DOI: 10.1055/s-0036-1591559
paper
Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts
This work was supported by the National Natural Science Foundation of China (Nos. 21572017 and 21772010).Further Information
Publication History
Received: 22 January 2018
Accepted after revision: 05 March 2018
Publication Date:
04 April 2018 (online)
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.
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.
- Supporting Information
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