Xerogel-Sequestered Silanated Organochalcogenide Catalysts for Bromination with Hydrogen Peroxide and Sodium Bromide

Gatley, Caitlyn M.; Muller, Lisa M.; Lang, Meredith A.; Alberto, Eduardo E.; Detty, Michael R.

doi:10.3390/molecules20069616

Open AccessArticle

Xerogel-Sequestered Silanated Organochalcogenide Catalysts for Bromination with Hydrogen Peroxide and Sodium Bromide

by

Caitlyn M. Gatley

^†,

Lisa M. Muller

^†,

Meredith A. Lang

,

Eduardo E. Alberto

and

Michael R. Detty

^*

Department of Chemistry, The State University of New York at Buffalo, Buffalo, NY 14260, USA

^*

Author to whom correspondence should be addressed.

^†

These authors contributed equally to this work.

Molecules 2015, 20(6), 9616-9639; https://doi.org/10.3390/molecules20069616

Submission received: 30 April 2015 / Accepted: 21 May 2015 / Published: 26 May 2015

(This article belongs to the Special Issue Selenium Catalysts and Antioxidants)

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Abstract

While H₂O₂ is a powerful oxidant, decomposing into environmentally benign H₂O and O₂, a catalyst is often required for reactions with H₂O₂ to proceed at synthetically useful rates. Organotellurium and organoselenium compounds catalyze the oxidation of halide salts to hypohalous acids using H₂O₂. When sequestered into xerogel monoliths, the xerogel-chalcogenide combinations have demonstrated increased catalytic activity relative to the organochalcogen compound alone in solution for the oxidation of halide salts to hypohalous acids with H₂O₂. Diorganotellurides, diorganoselenides, and diorganodiselenides bearing triethoxysilane functionalities were sequestered into xerogel monoliths and their catalytic activity and longevity were investigated. The longevity of the catalyst-xerogel combinations was examined by isolating and recycling the catalyst-xerogel combination. It was found tellurium-containing catalyst 3 and selenium-containing catalyst 8 maintained their catalytic activity through three recycling trials and adding electron-donating substituents to catalyst 3 also increased the catalytic rate. The presence of organotellurium and organoselenium groups in the +4 oxidation state was determined by X-ray photoelectron spectroscopy.

Keywords: organoselenides; organotellurides; diorgano diselenides; xerogel; catalytic bromination

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MDPI and ACS Style

Gatley, C.M.; Muller, L.M.; Lang, M.A.; Alberto, E.E.; Detty, M.R. Xerogel-Sequestered Silanated Organochalcogenide Catalysts for Bromination with Hydrogen Peroxide and Sodium Bromide. Molecules 2015, 20, 9616-9639. https://doi.org/10.3390/molecules20069616

AMA Style

Gatley CM, Muller LM, Lang MA, Alberto EE, Detty MR. Xerogel-Sequestered Silanated Organochalcogenide Catalysts for Bromination with Hydrogen Peroxide and Sodium Bromide. Molecules. 2015; 20(6):9616-9639. https://doi.org/10.3390/molecules20069616

Chicago/Turabian Style

Gatley, Caitlyn M., Lisa M. Muller, Meredith A. Lang, Eduardo E. Alberto, and Michael R. Detty. 2015. "Xerogel-Sequestered Silanated Organochalcogenide Catalysts for Bromination with Hydrogen Peroxide and Sodium Bromide" Molecules 20, no. 6: 9616-9639. https://doi.org/10.3390/molecules20069616

APA Style

Gatley, C. M., Muller, L. M., Lang, M. A., Alberto, E. E., & Detty, M. R. (2015). Xerogel-Sequestered Silanated Organochalcogenide Catalysts for Bromination with Hydrogen Peroxide and Sodium Bromide. Molecules, 20(6), 9616-9639. https://doi.org/10.3390/molecules20069616

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Xerogel-Sequestered Silanated Organochalcogenide Catalysts for Bromination with Hydrogen Peroxide and Sodium Bromide

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