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Synlett 2019; 30(14): 1698-1702
DOI: 10.1055/s-0037-1612083
cluster
© Georg Thieme Verlag Stuttgart · New York

Sodium Selenosulfate from Sodium Sulfite and Selenium Powder: An Odorless Selenylating Reagent for Alkyl Halides to Produce Dialkyl Diselenide Catalysts

Yonghong Liu
b   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
,
Hai Ling
b   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
c   Department of Chemistry, East China Normal University, Shanghai, 200062, P. R. of China   Email: xfjiang@chem.ecnu.edu.cn
,
Chao Chen
b   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
,
Qing Xu
b   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
,
Lei Yu  *
a   Guangling College, Yangzhou University, Yangzhou, Jiangsu 225000, P. R. of China   Email: yulei@yzu.edu.cn
b   School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China
,
Xuefeng Jiang  *
c   Department of Chemistry, East China Normal University, Shanghai, 200062, P. R. of China   Email: xfjiang@chem.ecnu.edu.cn
› Author AffiliationsThis work was supported by the Nature Science Foundation of Guangling College (ZKZZ18001).
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Publication History

Received: 12 November 2018

Accepted after revision: 26 December 2018

Publication Date:
07 February 2019 (online)

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Published as part of the Cluster Organosulfur and Organoselenium Compounds in Catalysis

Abstract

Na2SeSO3, which can be generated in situ by the reaction of Na2SO3 with Se power, was found to be an odorless reagent for the selenenylation of alkyl halides to produce dialkyl diselenides. These products have been recently shown to be good catalysts for the Baeyer–Villiger oxidation of carbonyl compounds, for the selective oxidation of alkenes, or for the oxidative deoximation of oximes. By using aqueous EtOH as the solvent and avoiding the generation of a malodourous selenol intermediate, the selenylation reaction with Na2SeSO3 is much more environmentally friendly than conventional methods. Owing to the cheap and abundant starting materials and selenium reagents, our novel synthetic method reduces the production costs of dialkyl diselenides as organoselenium catalysts, thereby advancing practical applications of organoselenium-catalysis technologies.

Key words

dialkyl diselenides - alkyl halides - selenenylation - organoselenium catalysts - green synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612083.
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