Directed Mizoroki–Heck Reactions

Oestreich, Martin

doi:10.1007/3418_2007_063

Cited by 39 publications

(16 citation statements)

References 72 publications

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“…[36][37][38] Über die letzten Jahrzehnte reifte dieser Prozess zu einer wertvollen Methode für die diastereoselektive Synthese von substituierten Alkenen. [39][40][41] So wurde beispielsweise kürzlich ein sehr aktives Katalysatorsystem für die oxidative Arylierung bei Umgebungstemperatur entwickelt (Schema 22). [42] Oxidative palladiumkatalysierte C-H-Funktionalisierungen beschränken sich nicht nur auf die direkte Arylierung von Alkenen, sondern erwiesen sich auch für C Aryl -C Aryl -Kupplungen als äußerst nützlich.…”

Section: Eisenkatalysierte Direkte Arylierungen Mit Metallorganischenunclassified

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

2009

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Das Gebiet der übergangsmetallkatalysierten direkten Arylierung unter C‐H‐Bindungsbruch hat in den letzten Jahren eine rasante Entwicklung erfahren, was dazu führte, dass sich solche Methoden immer mehr als Alternativen zu den herkömmlichen Kreuzkupplungen mit metallorganischen Reagentien etabliert haben. Insbesondere wurden zahlreiche Palladium‐ und Rutheniumkatalysatoren beschrieben, welche die direkte Arylierung von (Hetero)arenen mit anspruchsvollen Reaktionspartnern ermöglichen; hierzu gehören elektrophile Arylchloride und ‐tosylate oder auch einfache Arene in gekreuzten dehydrierenden Arylierungen.

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Section: Eisenkatalysierte Direkte Arylierungen Mit Metallorganischenunclassified

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

2009

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“…We utilise a series of well-known size and shape sensitive catalytic reactions which proceed via a well-established mechanism as a tool to probe the different reaction environments inside a GNF nanoreactor, and relate the observed activity and selectivity changes to the structure and the steric environment of the catalytic site. The Heck reaction -an arylhalide-arylalkene cross-coupling reaction catalysed by Pd catalysts [ 18 ] -gives a distribution of several isomeric coupling products, the selectivity of which depends strongly on the electronic and steric environment of the catalytic centre, [ 19 ] and is therefore an ideal reaction system to investigate the local reaction environment of catalyst materials. Variation of the size and shape of the reactant molecules by incorporating bulky planar and non-planar substituents, as well as modifying the size and shape of the catalyst molecule by using a square planar Pd(II)Salen complex and a modified Pd(II)Salen-C60, in which a bulky, spherical C60 cage is appended to the otherwise identical Pd(II)Salen complex, [ 20 ] results in notable changes of the catalyst activity and selectivity.…”

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confidence: 99%

Chemical reactions at the graphitic step-edge: changes in product distribution of catalytic reactions as a tool to explore the environment within carbon nanoreactors

et al. 2016

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A series of explorative cross-coupling reactions have been developed to investigate the local nanoscale environment around catalytically active Pd(II)complexes encapsulated within hollow graphitised nanofiber (GNF). Two new fullerene-containing and fullerene-free Pd(II)Salen catalysts have been synthesised, and their activity and selectivity towards different substrates has been explored in nanoreactors. The catalysts not only show a significant increase in activity and stability upon heterogenisation at the graphitic step-edges inside the GNF channel, but also exhibit a change in selectivity affected by the confinement which alters the distribution of isomeric products of the reaction. Furthermore, the observed selectivity changes reveal unprecedented details regarding the location and orientation of the catalyst molecules 2 inside the GNF nanoreactor, inaccessible by any spectroscopic or microscopic techniques, thus shedding light on the precise reaction environment inside the molecular catalyst-GNF nanoreactor.

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“…In this sense, palladiumnanoparticles (Pd-NPs) have been extensively employed as catalyst for the Heck reaction, since the pioneering work from Beller [115]. The major advantages related to the employment of metal nanoparticles in the Heck reaction include [116]: (i) high catalytic activity; (ii) excellent selectivity; and (iii) tolerance of water [117,118]. Bearing in mind these benefits of Pd-NP-catalyzed Heck reaction in water, Cacchi and co-workers reported a one-pot/two-step process connecting the aqueous Heck reaction with an enantioselective ADH-catalyzed bioreduction of the transiently-formed prochiral hydroxyl-ketone to produce the chiral alcohol (R)-(-)-rhododendrol (Scheme 23) [104].…”

Section: Combination Of Pd-catalyzed Heck Reaction Of Aryl Iodides Anmentioning

confidence: 99%

One-Pot Combination of Metal- and Bio-Catalysis in Water for the Synthesis of Chiral Molecules

2018

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During the last decade, the combination of different metal-and bio-catalyzed organic reactions in aqueous media has permitted the flourishing of a variety of one-pot asymmetric multi-catalytic reactions devoted to the construction of enantiopure and high added-value chemicals under mild reaction conditions (usually room temperature) and in the presence of air. Herein, a comprehensive account of the state-of-the-art in the development of catalytic networks by combining metallic and biological catalysts in aqueous media (the natural environment of enzymes) is presented. Among others, the combination of metal-catalyzed isomerizations, cycloadditions, hydrations, olefin metathesis, oxidations, C-C cross-coupling and hydrogenation reactions, with several biocatalyzed transformations of organic groups (enzymatic reduction, epoxidation, halogenation or ester hydrolysis), are discussed.

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Directed Mizoroki–Heck Reactions

Cited by 39 publications

References 72 publications

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

Chemical reactions at the graphitic step-edge: changes in product distribution of catalytic reactions as a tool to explore the environment within carbon nanoreactors

One-Pot Combination of Metal- and Bio-Catalysis in Water for the Synthesis of Chiral Molecules

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