Selenium‐Catalyzed debromination of <i>vic</i>‐dibromoalkanes and α‐bromo ketones with carbon monoxide and water

Since its original discovery over a century ago, the water-gas shift reaction (WGSR) has played a crucial role in industrial chemistry, providing a source of H2 to feed fundamental industrial transformations such as the Haber–Bosch synthesis of ammonia. Although the production of hydrogen remains nowadays the major application of the WGSR, the advent of homogeneous catalysis in the 1970s marked the beginning of a synergy between WGSR and organic chemistry. Thus, the reducing power provided by the CO/H2O couple has been exploited in the synthesis of fine chemicals; not only hydrogenation-type reactions, but also catalytic processes that require a reductive step for the turnover of the catalytic cycle. Despite the potential and unique features of the WGSR, its applications in organic synthesis remain largely underdeveloped. The topic will be critically reviewed herein, with the expectation that an increased awareness may stimulate new, creative work in the area.

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“…(24)]. [148] Similarly, achloroacetophenone undergoes dechlorination in the presence of PdCl 2 (PPh 3 ) 2 [Eq. (25)].…”

Section: Desulfurizationmentioning

confidence: 99%

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

Ambrosi

Denmark

2016

Angew Chem Int Ed

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“…Silber- [141] und Goldnanopartikel [142] auf einem Hydrotalcitträger sowie TiO 2 -gebundene Goldnanopartikel [143] (24)]. [148] Auf ähnliche Weise wird a-Chloracetophenon in Gegenwart von PdCl 2 -(PPh 3 ) 2 dechloriert [Gl. (25)].…”

Section: Desoxygenierung Von Epoxidenunclassified

Die Wassergas‐Shift‐Reaktion in der organischen Synthese

Ambrosi

Denmark

2016

Angewandte Chemie

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Seit ihrer Entdeckung vor mehr als hundert Jahren hat die Wassergas‐Shift‐Reaktion (WGSR) entscheidende Bedeutung in der industriellen Chemie, indem sie den Wasserstoff zur Beschickung grundlegender großtechnischer Prozesse wie der Haber‐Bosch‐Synthese von Ammoniak liefert. Obwohl die Produktion von Wasserstoff immer noch die Hauptanwendung der WGSR ist, markierte die Einführung der homogenen Katalyse in den 1970er Jahren den Beginn einer Synergie zwischen der WGSR und der organischen Chemie. Dabei wurde das Reduktionsvermögen des CO/H2O‐Paars in der Synthese von Feinchemikalien nicht nur für Hydrierungsreaktionen genutzt, sondern auch für katalytische Prozesse, deren Umsatz einen Reduktionsschritt im Katalysezyklus erfordert. Ungeachtet des Potenzials und der einzigartigen Eigenschaften der WGSR sind ihre Anwendungen in der organischen Synthese bisher noch wenig entwickelt. Dieses Thema wird hier kritisch besprochen in der Hoffnung, dass eine erhöhte Wahrnehmung zu neuen, kreativen Arbeiten auf dem Gebiet anregt.

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Organoselenium and Organotellurium Oxidation and Reduction

Młochowski

Lisiak

Wójtowicz‐Młochowska

2011

Patai's Chemistry of Functional Groups

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Oxygenated and reduced selenium and tellurium compounds, particularly thoese of practical importance have been extensively investigated especially during the last few decades. Selenium(IV) oxide, selenoxides, selenones, seleninic and peroxyseleninic acids, selenenamides and seleninamides are involved in oxyfunctionalization of unsaturated hydrocarbons, their derivatives, alkylarenes, sulfides and amines, carbon‐oxygen and carbon‐carbon bond cleavage, ring closure and ring transformations, syn ‐elimination, sigmatropic [2,3]‐rearrangement and other, chemo‐ regio‐ and stereocontrolled reactions. The chemistry of oxygenated tellurium compounds has been less extensively explored than their selenium counterparts;, nevertheless some of them have been successfully used for oxyfunctionalization of different groups of organic compounds while telluroxide elimination has gained more attention in the last years becoming a well‐established method for the synthesis of olefins. Hydrogen selenide and telluride, alkali selenides and tellurides, selenoles and telluroles are the most common reduced derivative of these elements. Their properties are expressed in many reactions such as reduction and deoxygenation of different groups of organic compounds alkenes, alkynes, ethers, carbonyl compounds, esters, lactones, oxiranes, nitrogen, sulfur and halogen compounds, as well as dealkylation of tertiary amines. The method for preparation of the different oxygenated and reduced selenium and tellurium compounds are described, their reactions are reviewed, their usefulness in synthesis is indicated and more representative mechanisms are discussed.

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Selenium‐Catalyzed debromination of vic‐dibromoalkanes and α‐bromo ketones with carbon monoxide and water

Abstract: Selenium has been found to be an excellent catalyst for the reductive debromination of some organic bromides with carbon monoxide and water: vic-dibromoalkanes and a-halo ketones can be reduced to the corresponding alkenes and ketones respectively in moderate to high yields.

Cited by 8 publications

References 53 publications

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

Die Wassergas‐Shift‐Reaktion in der organischen Synthese

Organoselenium and Organotellurium Oxidation and Reduction

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