Efficient Selenenylation of Malonates Using Bis(phosphorothioyl) Diselenide

Majewski, Arkadiusz; Przychodzeń, Witold; Rachoń, Janusz

doi:10.1080/10426507.2010.519253

Cited by 3 publications

(2 citation statements)

References 9 publications

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“…Our research was focused on the development of an effective method for electrophilic selenylation of indole rings. For this purpose we used bis( O , O ‐diisopropoxyphosphorothioyl) diselenide 1 , which we have previously shown to be an easy to handle and stable source of electrophilic selenium. The initial reactions were performed using O , O ‐diisopropoxyphosphorothioylselenyl bromide generated in‐situ in the reaction of 1 with bromine at –78 °C in DCM followed by its reaction with indole.…”

Section: Resultsmentioning

confidence: 99%

“…Bis( O , O ‐diisopropoxyphosphorothioyl) diselenide 1 used as selenium source is a crystalline, non‐hygroscopic, moisture‐, temperature‐, and light‐stable solid with a long shelf life (it can be stored on shelf for 10 years without significant traces of degradation). It is also easy to prepare from readily available O , O ‐diisopropyl H ‐phosphonate (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

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General, Mild, and Metal‐Free Functionalization of Indole and Its Derivatives Through Direct C3‐Selenylation

et al. 2019

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A very mild method for the introduction of functionalized alkylselenyl group at C‐3 position of the indole ring was developed. The proposed procedure consists of an electrophilic substitution of indole and its derivatives with bis(O,O‐diisopropoxyphosphorothioyl) diselenide and subsequent cleavage of the P–Se bond with tetrabutylammonium fluoride in the presence of various electrophilic reagents. This method can be successfully applied, inter alia, for the preparation of amino acid and glucoside derivatives of 3‐selenoindole.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

General, Mild, and Metal‐Free Functionalization of Indole and Its Derivatives Through Direct C3‐Selenylation

et al. 2019

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Medium-sized cyclic bis(anisylphosphonothioyl)disulfanes and their corresponding cyclic sulfane-structures and most characteristic reactions

2019

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Atom-economic thiophosphoroselenenylations of C–H acid esters and amides

Majewski

Przychodzeń

2021

Synthetic Communications

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SUPPORTING INFORMATION CONTENTS1. X-Ray diffraction 1 2. Characterization data of compounds 3 2 3. Copies of 1 H, 13 C, 31 P, and 77 Se NMR spectra of all new compounds 7 4. 31 P NMR monitoring of the P-Se bond splitting using TBAF 29 5. Crystal data and structure refinement for 3l (Table S1) 30 6. Two-dimensional intermolecular H-bonding network in 3l (Figure S58) 31 7. Cif file for 3l (CCDC 888468) 32 X-Ray diffractionThe experimental diffraction data were collected on a KM4CCD (Oxford Diffraction, now part of Varian) kappa-geometry diffractometer equipped with a Sapphire-2 area detector. An enhanced X-ray Mo Ka radiation source with a graphite monochromator was used. The data reduction was conducted using CrysAlis software package. 1 Structure solution and final refinement were carried out using the SHELX-97 program package. 2 Packing diagrams were prepared using Mercury visualization software. 3 The parameters of the crystal cell, the results of the refinement of the structure of 3l are shown in Table S1. Crystallographic data for compound 3l has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 888468. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.

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Efficient Selenenylation of Malonates Using Bis(phosphorothioyl) Diselenide

Cited by 3 publications

References 9 publications

General, Mild, and Metal‐Free Functionalization of Indole and Its Derivatives Through Direct C3‐Selenylation

General, Mild, and Metal‐Free Functionalization of Indole and Its Derivatives Through Direct C3‐Selenylation

Medium-sized cyclic bis(anisylphosphonothioyl)disulfanes and their corresponding cyclic sulfane-structures and most characteristic reactions

Atom-economic thiophosphoroselenenylations of C–H acid esters and amides

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