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

Yonghong Liu; Hai Ling; Chao Chen; Qing Xu; Lei Yu; Xuefeng Jiang

doi:10.1055/s-0037-1612083

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(14): 1698-1702
DOI: 10.1055/s-0037-1612083

cluster

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

Yonghong Liu

^bSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

,

Hai Ling

^bSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

^cDepartment of Chemistry, East China Normal University, Shanghai, 200062, P. R. of China eMail: xfjiang@chem.ecnu.edu.cn

,

Chao Chen

^bSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

,

Qing Xu

^bSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

,

Lei Yu *

^aGuangling College, Yangzhou University, Yangzhou, Jiangsu 225000, P. R. of China eMail: yulei@yzu.edu.cn

^bSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, P. R. of China

,

Xuefeng Jiang *

^cDepartment of Chemistry, East China Normal University, Shanghai, 200062, P. R. of China eMail: xfjiang@chem.ecnu.edu.cn

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

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

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Referenzen

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14 All reactions were performed in sealed tubes.
15 Dialkyl Diselenides 2a–m; General ProcedureA glass pressure-reaction tube equipped with a magnetic stirrer bar was charged with Na₂SO₃ (189.0 mg, 1.5 mmol), Se powder (118.5 mg, 1.5 mmol) and H₂O (2 mL). The tube was then filled with N₂ and sealed. The mixture was stirred at 140 °C for 48 h, and then cooled to r.t. A solution of the appropriate alkyl halide (1 mmol) in EtOH (1 mL) was added, and the tube filled with air and sealed. The mixture was heated in air at 100 °C for 48 h. The product was then isolated by preparative TLC (silica gel, PE).Dibutyl Diselenide (2a) ¹⁷Yellow oil; yield: 100.7 mg (74%). IR (film): 2956, 2924, 2853, 1461, 1377, 1287, 1251, 1210, 1179, 720 cm^–1. ¹H NMR (400 MHz, CDCl₃, TMS): δ = 2.95–2.87 (m, 4 H), 1.74–1.66 (m, 4 H), 1.44–1.37 (m, 4 H), 0.92 (t, J = 7.4 Hz, 6 H). ¹³C NMR (100 MHz, CDCl₃): δ = 33.0, 29.9, 22.6, 13.6.
16 MS (EI, 70 eV): m/z (%) = 274 (10) [M⁺], 57 (100).Characterization data and NMR spectra of all of the diselenide products are given in the Supporting Information.

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Zusatzmaterial

Supporting Information