7.28 Oxidation of Sulfur, Selenium, and Tellurium

Lattanzi, Alessandra

doi:10.1016/b978-0-08-097742-3.00734-5

Cited by 14 publications

(8 citation statements)

References 666 publications

(251 reference statements)

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“…On the basis of our analysis and literature precedence, ,− we propose the catalytic cycle outlined in Figure . Diselenide catalyst 8a is reduced by tributylphosphine to form selenophosphonium I , which associates rapidly with the carboxylate to form the pentacoordinated phosphorane II .…”

Section: Resultsmentioning

confidence: 89%

Rational Design of an Organocatalyst for Peptide Bond Formation

et al. 2019

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Amide bonds are ubiquitous in peptides, proteins, pharmaceuticals, and polymers. The formation of amide bonds is a straightforward process: amide bonds can be synthesized with relative ease because of the availability of efficient coupling agents. However, there is a substantive need for methods that do not require excess reagents. A catalyst that condenses amino acids could have an important impact by reducing the significant waste generated during peptide synthesis. We describe the rational design of a biomimetic catalyst that can efficiently couple amino acids featuring standard protecting groups. The catalyst design combines lessons learned from enzymes, peptide biosynthesis, and organocatalysts. Under optimized conditions, 5 mol % catalyst efficiently couples Fmoc amino acids without notable racemization. Importantly, we demonstrate that the catalyst is functional for the synthesis of oligopeptides on solid phase. This result is significant because it illustrates the potential of the catalyst to function on a substrate with a multitude of amide bonds, which may be expected to inhibit a hydrogen-bonding catalyst.

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Section: Resultsmentioning

confidence: 89%

Rational Design of an Organocatalyst for Peptide Bond Formation

et al. 2019

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“…Since both of them are only moderately active toward most organic substrates, various promoters are used, among them, selenium compounds transferring oxygen atoms from primary oxygen donor to oxidized substrate [11,12,13,14,15,16,17,18]. The oxidation of organoselenium (also organotellurium and sulfur) compounds to diselenides, selenones, selenoxides, seleninic acids and other derivatives are illustrated in several books [9,19].…”

Section: Introductionmentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

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A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as "green reagents" for the oxidation of different organic functional groups. The topic of oxidations catalyzed by organoselenium derivatives has rapidly expanded in the last fifteen years This paper is devoted to the synthetic applications of the oxidation reactions mediated by selenium compounds such as selenium(IV) oxide, areneseleninic acids, their anhydrides, selenides, diselenides, benzisoselenazol-3(2H)-ones and other less often used other organoselenium compounds. All these compounds have been successfully applied for various oxidations useful in practical organic syntheses such as epoxidation, 1,2-dihydroxylation, and α-oxyfunctionalization of alkenes, as well as for ring contraction of cycloalkanones, conversion of halomethyl, hydroxymethyl or active methylene groups into formyl groups, oxidation of carbonyl compounds into carboxylic acids and/or lactones, sulfides into sulfoxides, and secondary amines into nitrones and regeneration of parent carbonyl compounds from their azomethine derivatives. Other reactions such as dehydrogenation and aromatization, active carbon-carbon bond cleavage, oxidative amidation, bromolactonization and oxidation of bromide for subsequent reactions with alkenes are also successfully mediated by selenium (IV) oxide or organoselenium compounds. The oxidation mechanisms of ionic or free radical character depending on the substrate and oxidant are discussed. Coverage of the literature up to early OPEN ACCESSMolecules 2015, 20 10206 2015 is provided. Links have been made to reviews that summarize earlier literature and to the methods of preparation of organoselenium reagents and catalysts.

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“…The oxidation of sulfides is one of the oldest but still widely employed methods for the synthesis of sulfones. [11a] Moreover, sulfide oxidation is performed on an enormous annual scale in the oxidative desulfurization, a process for the removal of sulfur compounds from crude oil. [11b] Therefore, new approaches to improve the overall efficiency and sustainability of sulfide oxidation are still receiving great attention.…”

Section: Synthesis Via the Oxidation Of Sulfidesmentioning

confidence: 99%

Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones

et al. 2021

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Sulfones play a pivotal role in modern organic chemistry. They are highly versatile building blocks and find various applications as drugs, agrochemicals, or functional materials. Therefore, sustainable access to this class of molecules is of great interest. Herein, the goal was to provide a summary on recent develop-ments in the field of sustainable sulfone synthesis. Advances and existing limitations in traditional approaches towards sulfones were reviewed on selected examples. Furthermore, novel emerging technologies for a more sustainable sulfone synthesis and future directions were discussed.

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7.28 Oxidation of Sulfur, Selenium, and Tellurium

Cited by 14 publications

References 666 publications

Rational Design of an Organocatalyst for Peptide Bond Formation

Rational Design of an Organocatalyst for Peptide Bond Formation

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones

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