Fe(III)-Catalyzed direct C3 chalcogenylation of indole: The effect of iodide ions

Luz, Eduardo Q.; Seckler, Diego; Araújo, Janylson Souza; Angst, Leonardo; Lima, David B.; Rios, Elise Ane Maluf; Ribeiro, Ronny R.; Rampon, Daniel S.

doi:10.1016/j.tet.2019.01.037

Cited by 30 publications

(21 citation statements)

References 145 publications

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“…Because of the very large shift range for 77 Se, a separate search for each specific region of the larger spectral window may be required, minimizing pulse distortion. Therefore, based on the outcomes of the 77 Se NMR spectra, it is important to describe in the manuscript all the tests that were carried out, even if the analyses have failed [74,75,76] . These information can be useful for further investigations.…”

Section: Se Nmr Spectroscopy In Organic Synthesismentioning

confidence: 99%

“…However, 77 Se NMR analysis does not always provide satisfactory results. Depending on the stability, [74] or the kinetic process quickness, [75] the acquisition of 77 Se NMR spectra can be hampered. Because of the very large shift range for 77 Se, a separate search for each specific region of the larger spectral window may be required, minimizing pulse distortion.…”

Section: Se Nmr Spectroscopy In Organic Synthesismentioning

confidence: 99%

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Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

et al. 2020

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This review article deals with organic synthesis from the perspective of selenium-77 nuclear magnetic resonance (NMR) spectroscopy. Different types of organic reactions are briefly discussed, incorporating mechanism aspects through 77 Se NMR observable intermediates and byproducts. The 77 Se NMR experiments are demonstrated in terms of structural characterization and new insights for organic reactions. The ability to visualize different molecules in a reaction mixture provides a facile and versatile route for the development of synthetic organoselenium compounds. Thus, the review describes the strategies accomplished mainly in the past five years in the syntheses and applications of the organoselenium compounds, focusing on 77 Se NMR spectroscopy.

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Section: Se Nmr Spectroscopy In Organic Synthesismentioning

confidence: 99%

Section: Se Nmr Spectroscopy In Organic Synthesismentioning

confidence: 99%

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

et al. 2020

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“…A vast array of methods [9] for synthesis of 3‐selenylindoles have been demonstrated employing metal salts (e. g. FeCl 3 , [10] CuI [11] ), bases [12,13] or oxidants [14–16] . More sustainable methods have been developed based on electrochemically‐induced process [17,18] …”

Section: Introductionmentioning

confidence: 99%

Visible Light‐Mediated Functionalization of Selenocystine‐Containing Peptides

et al. 2021

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A straightforward and atom‐economic method for the functionalization of short selenocystine‐containing peptides is presented. This method is shown to be tolerant to unprotected peptides. The detailed protocol is based on the generation of a selenium radical via visible light‐initiated reaction in the presence of transition metal‐free photocatalyst. The selenium radical is further oxidized to an electrophile and trapped by N‐heterocycles. The mechanism is confirmed by NMR, HRMS, UV, EPR and cyclic voltammetry (CV) experiments and photocatalyst emission quenching studies. A visible light‐initiated reaction is employed for the synthesis of selenocysteine‐containing indole‐based macrocycles via intramolecular Se−C bond formation.

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“…Over the past few years, synthetic methods for the preparation indoyl selenides have been drastically improved, but the reaction of indole with diorganyl diselenide in the basic conditions remains the most common pathway . Other commonly used selenylation methods are electrophilic substitution with organoselenium halides or phthalimides and copper‐catalyzed reaction with diorganyl diselenides . However, despite of their advantages, this methods have one common drawback: all methods require the usage of diaryl or dialkyl diselenides, and especially the preparation of the latter might be the major challenge of the synthetic procedure.…”

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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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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Fe(III)-Catalyzed direct C3 chalcogenylation of indole: The effect of iodide ions

Cited by 30 publications

References 145 publications

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

Visible Light‐Mediated Functionalization of Selenocystine‐Containing Peptides

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

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