Monomeric ruthenium carbonyls containing 2-substituted pyrazinesFrom synthesis to catalytic activity in 1-hexene hydroformylation

Moreno, M. Andreina; Haukka, Matti; Turunen, Anniina; Pakkanen, Tapani A.

doi:10.1016/j.molcata.2005.06.028

Cited by 34 publications

(17 citation statements)

References 30 publications

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“…188 During the reaction both aldehydes and alcohols are formed revealing that hydroformylation is followed by the hydrogenation of the aldehydes.…”

Section: 187mentioning

confidence: 99%

Computational aspects of hydroformylation

Kégl

2015

RSC Adv.

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The influence of transition metal complexes as catalysts upon the activity and selectivity of hydroformylation reactions has been extensively investigated during the last decades. Nowadays computational chemistry is an indispensable tool for elucidation of reaction mechanisms and for understanding the various aspects which govern the outcome of catalytic reactions. This review attempts to survey the recent literature concerning computational studies on hydroformylation and theoretical coordination chemistry results related to hydroformylation.

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“…188 During the reaction both aldehydes and alcohols are formed revealing that hydroformylation is followed by the hydrogenation of the aldehydes.…”

Section: 187mentioning

confidence: 99%

Computational aspects of hydroformylation

Kégl

2015

RSC Adv.

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“…[16][17][18] Peethala et al, 19 Turk et al, 20 and several others [21][22][23][24][25] have previously investigated the CMP of Ru and Cu films as well as the galvanic corrosion behavior of the Ru/Cu couple in the presence of potassium periodate, sodium percarbonate and other oxidizers. Recently, Amanapu et al 15 [26][27][28][29] Thus, Ru oxides and hydroxides, but not Ru, in the presence of GC are likely to form complexes through interaction of -electrons on the nitrogen atoms of the guanidinium ions. The binding between these highly electronegative nitrogen atoms and Ru in these complexes can partially polarize the underlying Ru-Ru bonds and weaken them sufficiently to cause rupture during polishing and lead to an increase in the polish rate.…”

mentioning

confidence: 99%

Investigation of Guanidine Carbonate-Based Slurries for Chemical Mechanical Polishing of Ru/TiN Barrier Films with Minimal Corrosion

Sagi

Amanapu

Teugels

et al. 2014

ECS J. Solid State Sci. Technol.

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This work describes the response of Ru/TiN barrier films to solutions of H 2 O 2, guanidine carbonate (GC) and other additives in terms of open circuit potential measurements and potentiodynamic polarization data. It was found that an aqueous solution containing 1 wt% H 2 O 2 , 0.25 wt% GC and 5 mM BTA is effective in maintaining a low corrosion potential gap of Ru and Cu at ∼15 mV at pH 9. The slurry prepared by adding 5 wt% silica to this mixture yields a Ru removal rate (RR) of 10 nm/min and a Cu RR of 12 nm/min at 2 psi polishing pressure. The effect of carbonate and guanidinium ions as well as BTA on the corrosion behavior of Ru and Cu is discussed. Dodecyl-benzene-sulfonic acid (DBSA) was also found to be an effective corrosion inhibitor of Ru in the presence of H 2 O 2 and GC based solutions at pH 9 with a good post-polished surface finish but reduced the Ru RRs to ∼ 2 nm/min. As the scaling of interconnect structures continues beyond the 22 nm technology node, the width of copper lines continues to diminish. At such lower line widths, the effect of electron scattering on conductivity increases resulting in higher resistivity and reduced current carrying capacity. One way of mitigating this effect is to reduce the barrier liner thickness to less than ∼3 nm to accommodate a thicker copper line within a given trench. In such situations, the Ta/TaN bilayer, commonly used as barrier liner in the earlier copper interconnects, 1-4 faces several challenges. These include an inability to conformally deposit a thin barrier film in the high aspect ratio trenches which inevitably leads to void formation in the subsequently deposited copper seed layer. To surmount such challenges, Ruthenium (Ru) and several of its alloys have been proposed as alternative barrier liners.5-10 These have the added advantage of direct electroplating of Cu, eliminating the need for a Cu seed layer.However, Ru is not an ideal barrier as it forms columnar structures and, hence, provides diffusion paths for Cu at the grain boundaries 11,12 and also has poor adherence to the underlying dielectrics which may result in the peeling of these films during polishing.13,14 Therefore, a thin (∼1 nm) TaN or TiN layer is deposited between Ru and the dielectric interface which helps in both negating the columnar growth of Ru and improving the adherence between Ru and the dielectric. 13,14 Of these, Ru/TiN structures were chosen for the analysis here since Amanapu et al. 15 have shown that these films are polished faster compared to those on TaN. They attributed this to the difference in the crystalline orientation of the Ru films deposited on TiN and TaN layers.It is very difficult to obtain adequate removal rates (RR) of Ru during planarization since it is a noble and hard material, making it a challenge to achieve the desired RR selectivity to Cu at the barrier interface. Moreover, Ru is more cathodic to Cu since its standard reduction potential (0.21 V vs. SCE) is greater than that of Cu (0.1 V vs. SCE). Hence, there is a high possibility of Cu corro...

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“…Eine Erhçhung des sterischen Anspruchs in 2-Position führt, so von den Autoren vermutet, zu einer Stabilisierung der monomeren Spezies und unterdrückt die Bildung des katalytisch weniger aktiven Ru-pz-Ru-Dimers. [45] [44] Abbildung 4. Carbonylrutheniumkomplexe von Triphenylphosphinliganden mit koordinationsfähigen ortho-Substituenten.…”

Section: Angewandte Aufsätzeunclassified

Alternative Metalle für die homogen katalysierte Hydroformylierung

et al. 2013

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Die Übergangsmetall‐katalysierte Hydroformylierung ist eine der effizientesten Methoden zur C‐C‐Bindungsknüpfung in der organischen Synthesechemie und repräsentiert eines der bedeutendsten Beispiele der Anwendung homogener Katalyse im großtechnischen Maßstab. Die Umsetzung von breit verfügbaren ungesättigten Kohlenwasserstoffen mit Kohlenstoffmonoxid und Wasserstoff zu den entsprechenden höheren Aldehyden ist sowohl synthesetechnisch als auch ökonomisch von großem Wert. Die entstehenden Aldehyde dienen als Grundstoffe für zahlreiche Folgeprodukte und werden jährlich im Millionen‐Tonnen‐Maßstab zu Weichmachern, Detergenzien und Tensiden umgesetzt. Industrielle Hydroformylierungsprozesse basieren derzeit größtenteils auf der Verwendung von Rhodium als Katalysatormetall. Aufgrund der steigenden Nachfrage nach diesem kostspieligen Metall wächst das Interesse am Einsatz kostengünstigerer, alternativer Metallkatalysatoren. Der folgende Aufsatz fasst die Entwicklung der Verwendung von Ru‐, Ir‐, Pd‐ und Fe‐Katalysatoren in der Hydroformylierung zusammen.

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Monomeric ruthenium carbonyls containing 2-substituted pyrazinesFrom synthesis to catalytic activity in 1-hexene hydroformylation

Cited by 34 publications

References 30 publications

Computational aspects of hydroformylation

Computational aspects of hydroformylation

Investigation of Guanidine Carbonate-Based Slurries for Chemical Mechanical Polishing of Ru/TiN Barrier Films with Minimal Corrosion

Alternative Metalle für die homogen katalysierte Hydroformylierung

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