Metal-catalyzed carbonylation of alkynes: key aspects and recent development

Quintero-Duque, Samuel; Dyballa, Katrin M.; Fleischer, Ivana

doi:10.1016/j.tetlet.2015.04.043

Cited by 60 publications

(12 citation statements)

References 182 publications

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“…However, the simultaneous formation of nickel(0) carbonyl complexes such as [Ni(CO) 3 L] was inevitable . The formation of a nickel(0) species from nickel(0) carbonyl complexes, which promote the oxidative cyclization, is generally challenging in the presence of CO gas, and the development of a nickel(0)‐catalyzed carbonylative cycloaddition with CO gas itself might thus be hampered . To overcome this limitation, we employed phenyl formate as a CO source to regulate the concentration of CO, as it has to be sufficiently high for the reaction with the nickelacycle intermediates, yet also sufficiently low to ensure the formation of [Ni(CO) 3 L].…”

Section: Methodsmentioning

confidence: 99%

Efficient Synthesis of Polycyclic γ‐Lactams by Catalytic Carbonylation of Ene‐Imines via Nickelacycle Intermediates

et al. 2017

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The nickel(0)-catalyzed carbonylative cycloaddition of 1,5- and 1,6-ene-imines with carbon monoxide (CO) is reported. Key to this reaction is the efficient regeneration of the catalytically active nickel(0) species from nickel carbonyl complexes such as [Ni(CO) L]. A variety of tri- and tetracyclic γ-lactams were thus prepared in excellent yields with 100 % atom efficiency. Preliminary results on asymmetric derivatives promise potential in the synthesis of enantioenriched polycyclic γ-lactams.

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Section: Methodsmentioning

confidence: 99%

Efficient Synthesis of Polycyclic γ‐Lactams by Catalytic Carbonylation of Ene‐Imines via Nickelacycle Intermediates

et al. 2017

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Section: The Water-gas Shift Reaction In Organic Synthesismentioning

confidence: 99%

“…Alarge number of carbonylation reactions are carried out using mixtures of CO and H 2 O, namely hydroxycarbonylation of alkenes, [176] alkynes, [177] and halides [47b] (including the Monsanto process). [178] However,acareful distinction must be made as to the role of CO and H 2 O. Thea forementioned transformations are redox-neutral and employ CO and H 2 O as reactants,not as areducing couple.Since the WGSR is not involved, those transformations will not be covered here.…”

Section: Other Carbonylation Reactionsmentioning

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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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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“…Sehr viele Carbonylierungsreaktionen wurden mit Gemischen aus CO und H 2 Od urchgeführt, darunter die Hydroxycarbonylierung von Alkenen, [176] Alkinen [177] und Halogeniden [47b] (einschließlich dem Monsanto-Prozess). [178] 12 unter basischen Bedingungen zu Furanonen (Abbildung 13 a).…”

Section: Andere Carbonylierungsreaktionenunclassified

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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Metal-catalyzed carbonylation of alkynes: key aspects and recent development

Cited by 60 publications

References 182 publications

Efficient Synthesis of Polycyclic γ‐Lactams by Catalytic Carbonylation of Ene‐Imines via Nickelacycle Intermediates

Efficient Synthesis of Polycyclic γ‐Lactams by Catalytic Carbonylation of Ene‐Imines via Nickelacycle Intermediates

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

Die Wassergas‐Shift‐Reaktion in der organischen Synthese

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