Ruthenium-catalysed codimerisation of myrcene with methyl acrylate: Catalyst screening and mechanistic discussions

Behr, Arno; Johnen, Leif; Rentmeister, Nils

doi:10.1016/j.apcata.2012.12.020

Cited by 5 publications

(5 citation statements)

References 32 publications

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“…The compound 134 is an analogue of pyrrolostatin, a lipid peroxidation inhibitor. 2,5-Dihydrofuran 68 also reacts with β-myrcene to give a congener of dendrolasin 135 , a marine franoterpenoid . Unfortunately, simple acrylate and acrylamide did not react with heterocyclic five-membered rings.…”

Section: Cross-dimerizations Using Substituted Alkenesmentioning

confidence: 99%

Recent Advances in the Catalytic Linear Cross-Dimerizations

Hirano

2019

ACS Catal.

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Catalytic cross-dimerization is one of the powerful synthetic methods to produce linear molecules with high atom and step economy. Because this process involves a carbon–carbon-bond-forming reaction, enantioselective reactions have also been achieved. The most well-reviewed area in this field is probably hydrovinylation using ethylene, but the linear cross-dimerizations using substituted alkenes and alkynes have also been extensively developed. Not only do the products vary depending on these substrates, but they mostly differ from hydrovinylation in the mechanism. This Perspective presents a comprehensive summary on the basis of these substrates, including their brief historical background, mechanism, applications to the synthesis of biologically active compounds or contributions to the total synthesis, and the state-of-the-art advancements. The controlling factors in the chemo- and regioselectivities are also discussed.

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Section: Cross-dimerizations Using Substituted Alkenesmentioning

confidence: 99%

Recent Advances in the Catalytic Linear Cross-Dimerizations

Hirano

2019

ACS Catal.

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“…Branched C11‐esters were obtained in 61 % yields by palladium catalyzed methoxycarbonylation, as well as by ruthenium catalyzed cross metathesis with methyl acrylate . However, ruthenium catalyzed codimerization with methyl acrylate yields different C13‐esters (Figure ) …”

Section: C6 Molecules (Renewables)mentioning

confidence: 99%

“…[105] However, ruthenium catalyzed codimerization with methyl acrylate yields different C13-esters ( Figure 45). [106]…”

Section: Carbonylationmentioning

confidence: 99%

Homogeneously Catalyzed 1,3‐Diene Functionalization – A Success Story from Laboratory to Miniplant Scale

et al. 2018

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For many years, the efficient use of resources has been a major and permanent challenge for the chemical industry. The implementation of alternative resources such as renewables and carbon dioxide has been a subject of considerable discussion, but also the more efficient use of long known bulk chemicals is of great interest. Among them, 1,3‐dienes such as 1,3‐butadiene from the C4 cut of the naphtha cracker as well as isoprene, piperylene and cyclopentadiene from the corresponding C5 section are important substrates. These dienes are presently employed in various markets, with the greatest importance being in the production of polymers and copolymers. However, homogeneous transition metal catalysis has proven to be a versatile tool to functionalize these important 1,3‐dienes to low molecular weight fine chemicals by introducing, for example, nitrogen, oxygen or silicon. Hence, an upgraded use of the corresponding products as agrochemicals, pharmaceuticals, fragrances or special detergents is close at hand. The main approaches in the topic of homogeneous functionalization reactions of the industrially relevant 1,3‐dienes will be summarized and discussed within the present article. Besides that, novel applications including renewable 1,3‐dienes, for example β‐myrcene and β‐farnesene, as well as the application of CO2 in telomerization, will be critically discussed.

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“…Interessante funktionalisierte Verbindungen ergeben sich durch die Cooligomerisierung ungesättigter Verbindungen mit Methylacrylat, z. B. bei Umsetzungen mit Ethen 151 oder Myrcen 152. Erwähnt sei auch noch ein aktueller Übersichtsbeitrag zur C–C‐Kupplung mit Ethen 153.…”

Section: Neue Entwicklungen In Der Hükunclassified

Neue Trends in der homogenen Übergangsmetallkatalyse

Behr

Vorholt

2014

Chemie Ingenieur Technik

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zum 80. Geburtstag gewidmet Dieser Beitrag gibt eine ausgewählte Ü bersicht über aktuelle Entwicklungen in der homogenen Ü bergangsmetallkatalyse. Im Vordergrund stehen hier vor allem technisch relevante Reaktionen, wie z. B. Hydroformylierung, Carbonylierung, Hydrierung, Oxidation, Aminierung, Metathese und resultierende Tandemreaktionen. Neben dem Einsatz klassischer petrochemischer Grundstoffe wird ebenfalls die Umsetzung nachwachsender Rohstoffe diskutiert. An ausgewählten Beispielen werden kontinuierlich durchgeführte Umsetzungen der Reaktionen in Miniplants gezeigt.This contribution presents an overview of current developments in homogeneous catalysis. In this respect, the focus lies on industrial relevant reactions like hydroformylation, carbonylation, hydrogenation, oxidation, amination and metathesis and resulting tandem reactions. Beyond the classical petrochemical feedstocks, also renewables such as a sustainable feedstock are discussed. Selected examples of homogeneous catalysis in continuously operated miniplants are given.

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Ruthenium-catalysed codimerisation of myrcene with methyl acrylate: Catalyst screening and mechanistic discussions

Cited by 5 publications

References 32 publications

Recent Advances in the Catalytic Linear Cross-Dimerizations

Recent Advances in the Catalytic Linear Cross-Dimerizations

Homogeneously Catalyzed 1,3‐Diene Functionalization – A Success Story from Laboratory to Miniplant Scale

Neue Trends in der homogenen Übergangsmetallkatalyse

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