Amidation of chloroalkenes catalyzed by tertiary phosphine complexes of palladium(0)

Nicholas, Paul P.

doi:10.1021/jo00232a038

Cited by 29 publications

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“…PtBu 3 was introduced to Pd-mediated cross coupling chemistry in 1987 by Nicholas in the amidation of vinyl chloride. 82 In various coupling reactions such as Suzuki-Miyaura, 55 108 and cyanation, 109 the palladium complexes of PtBu 3 demonstrated their excellent performance.…”

Section: A Global View On the Role Of Trialkylphosphines In Cross Coumentioning

confidence: 99%

Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

2010

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The strong electron-donation and the steric bulk of trialkylphosphines renders them as very useful ligands for palladium-catalyzed cross coupling reactions. This critical review reports on the synthesis of two families of trialkylphosphines (diadamantylalkylphosphines, fluorenyldialkylphosphines) and the properties of the respective palladium complexes in various cross coupling reactions, which evolved as alternatives to the classical Pd/PtBu(3) system. In contrast to the latter phosphine the new classes of ligands are characterized by a highly flexible ligand design, which allows the fine tuning of catalytic properties to the specific needs of certain substrates and also enables the attachment of additional tags to impart certain useful properties onto the respective phosphines (179 references).

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Section: A Global View On the Role Of Trialkylphosphines In Cross Coumentioning

confidence: 99%

Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

2010

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“…[124] Fu und Koie wendeten Pd/PtBu 3 -Katalysatorsysteme daraufhin auch in Kupplungsreaktionen mit unaktivierten Substraten wie Arylchloriden an. [124] Fu und Koie wendeten Pd/PtBu 3 -Katalysatorsysteme daraufhin auch in Kupplungsreaktionen mit unaktivierten Substraten wie Arylchloriden an.…”

Section: Die Bedeutung Der Liganden Und Ihrer Eigenschaftenunclassified

“…[115] Palladiumkatalysierte Kreuzkupplungen Angewandte Chemie Schon vor Osborns Beobachtungen hatte Nicholas das pyrophore PtBu 3 in der palladiumkatalysierten carbonylierenden Amidierung von Vinylchloriden eingesetzt. [124] Fu und Koie wendeten Pd/PtBu 3 -Katalysatorsysteme daraufhin auch in Kupplungsreaktionen mit unaktivierten Substraten wie Arylchloriden an. [125] Fus erste Verçffentlichung [125a] lçste im Jahr 1998 in akademischer und industrieller Forschung ein erneutes Interesse an diesen Reaktionen aus, das zu einer starken Zunahme der Ligandenvariationsstudien im vergangenen Jahrzehnt führte.…”

Section: Die Bedeutung Der Liganden Und Ihrer Eigenschaftenunclassified

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Palladiumkatalysierte Kreuzkupplungen: eine historische Perspektive im Kontext der Nobel‐Preise 2010

et al. 2012

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Im Jahr 2010 wurden Richard Heck, Ei‐ichi Negishi und Akira Suzuki in den illustren Kreis der Chemie‐Nobelpreisträger aufgenommen. Begründet wurde diese Auszeichnung mit ihrer Rolle bei der Entdeckung und Entwicklung von praktischen Methoden zur C‐C‐Bindungsbildung. Ausgelöst durch ihre Beiträge über höchst nützliche palladiumkatalysierte Kreuzkupplungen, hat sich seit den frühen 1970er Jahren die Auswahl an verfügbaren Strategien und Methoden in der modernen organischen Synthese grundlegend verändert – sowohl für Chemiker an Hochschulen wie auch in der Industrie. Dieser Aufsatz vollzieht die historische Entwicklung dieser leistungsstarken Reaktionen nach: von den bahnbrechenden Entdeckungen bis hin zu den Kreuzkupplungsverfahren, die heute in der Synthese angewendet und hoch geschätzt werden.

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“…[1] This approach has successfully been adopted in labelling reactions with very low concentrations of [ 11 C]carbon monoxide. [2] However, previously reported syntheses of 11 C-labelled amides using [ 11 C]carbon monoxide have not included acrylamides. [3] Compounds labelled with 11 C, a β + -emitting radionuclide with a half-life of 20.4 min, are used as radiotracers in molecular imaging in vivo by positron emission tomography (PET).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of [¹¹C]/[¹³C]Acrylamides by Palladium‐Mediated Carbonylation

2007

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Two methods are presented for the synthesis of acrylamides labelled with 11C (β+, t1/2 = 20.4 min) and 13C in the carbonyl position. In the first method, [1‐11C]acrylic acid is synthesised from [11C]carbon monoxide by palladium‐mediated hydroxycarbonylation of acetylene. The labelled carboxylic acid is converted into the acyl chloride and subsequently treated with amine to yield N‐benzyl[carbonyl‐11C]acrylamide. The second method utilizes [11C]carbon monoxide in a palladium‐mediated carbonylative cross‐coupling of vinyl halides and amines. A higher radiochemical yield is achieved with the latter method and the amount of amine needed is decreased to 1/20. The 11C‐labelled acrylamides were isolated in up to 81 % decay‐corrected radiochemical yield. Starting from 10 ± 0.5 GBq of [11C]carbon monoxide, N‐benzyl[carbonyl‐11C]acrylamide was obtained in 4 min with a specific radioactivity of 330 ± 4 GBq μmol–1. Co‐labelling with 11C and 13C enabled confirmation of the labelled position by 13C NMR spectroscopy. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Amidation of chloroalkenes catalyzed by tertiary phosphine complexes of palladium(0)

Cited by 29 publications

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Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

Palladiumkatalysierte Kreuzkupplungen: eine historische Perspektive im Kontext der Nobel‐Preise 2010

Synthesis of [¹¹C]/[¹³C]Acrylamides by Palladium‐Mediated Carbonylation

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Amidation of chloroalkenes catalyzed by tertiary phosphine complexes of palladium(0)

Cited by 29 publications

References 0 publications

Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

Palladiumkatalysierte Kreuzkupplungen: eine historische Perspektive im Kontext der Nobel‐Preise 2010

Synthesis of [11C]/[13C]Acrylamides by Palladium‐Mediated Carbonylation

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Synthesis of [¹¹C]/[¹³C]Acrylamides by Palladium‐Mediated Carbonylation