Tandem ROMP−Hydrogenation with a Third-Generation Grubbs Catalyst

Camm, Kenneth D.; Castro, Nemesio Martinez; Liu, Yuwen; Czechura, Pawel; Snelgrove, Jennifer L.; Fogg, Deryn E.

doi:10.1021/ja071047o

Cited by 103 publications

(68 citation statements)

References 28 publications

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“…[4,5] Complex 2, used either directly or generated in situ, is among the most efficient catalysts in current use for the reduction of C=C bonds in nitrile-butadiene polymers [5][6][7][8] and unsaturated polymers derived from ringopening metathesis polymerization (ROMP). [9,10] Its recent applications to molecular transformations span a wide range of applications. Reactions of alkenes range from hydrogenation [11,12] and isomerization, [11,13] to diverse addition and coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Improved Syntheses of Versatile Ruthenium Hydridocarbonyl Catalysts Containing Electron‐Rich Ancillary Ligands

et al. 2008

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Section: Introductionmentioning

confidence: 99%

Improved Syntheses of Versatile Ruthenium Hydridocarbonyl Catalysts Containing Electron‐Rich Ancillary Ligands

et al. 2008

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“…In a previous paper, we reported on a catalytic system consisting of WCl 6 , iso-Bu 3 Al, and EtOH, and showed that it was highly effective for the ROMP polymerization of tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodec-3-ene (TCD). The yield of the ROMP polymer and the degree of gel formation were significantly affected by the concent- .1…”

Section: Resultsmentioning

confidence: 99%

“…4,[10][11][12] In spite of high activity of these catalysts, Ru-catalyzed hydrogenation has a serious drawback in terms of product purification due to contamination by hard-to-remove Ru complexes and low molecular weight side products formed from the polymer chain scission reaction.…”

Section: -4mentioning

confidence: 99%

“…With the hope of gaining insight into directions for the development of high performance heterogeneous catalysts ROMP polymers, we carried out a detailed investigation of various factors affecting the hydrogenation reactions of the ROMP polymer (p-Et-TCD) obtained from ethyl-substituted tetracyclododecene (8-ethyl-tetracyclo[4.4.0.1 2,5 .1 7,10 ] dodec-3-ene (Et-TCD) (Fig. 1).…”

Section: 20mentioning

confidence: 99%

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Ring-Opening Metathesis Polymerization and Hydrogenation of Ethyl-substituted Tetracyclododecene

Kwon¹,

Vo²,

Lee³

et al. 2011

Bulletin of the Korean Chemical Society

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Ring-opening metathesis polymerization (ROMP) of an ethyl-substituted tetracyclododecene (8-ethyltetracyclo[4.4.0.1 2,5 .1 7,10] dodec-3-ene, Et-TCD) was carried out in the presence of a ternary catalyst system consisting of WCl 6 , triisobutyl aluminium (iso-Bu 3 Al), and ethanol. The optimal molar ratio of Et-TCD/WCl 3 / iso-Bu 3 Al/ethanol was found as 500/1/3/2 at which the yield of ring-opened polymer was 100%. 1-Hexene was shown to be an effective molecular weight controlling agent for ROMP reaction of Et-TCD. The hydrogenation of the ring opened polymer (p-Et-TCD) was conducted successfully using Pd(5 wt %)/γ-Al 2 O 3 at 80 o C for 1 h. Chemical structures of p-Et-TCD and its hydrogenated product(H 2 -p-Et-TCD) were characterized using 2D NMR techniques ( H- 13C HSQC). The changes of physical properties such as thermal stability, glass transition temperature and light transmittance after the hydrogenation were also investigated using TGA, DSC, and UV.

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“…Assisted tandem catalysis is a method that employs a single catalyst to perform multiple transformations. Ruthenium metathesis catalysts have been utilized in transformations as C-C bond forming agents that can promote additional structural elaborations [162][163][164][165][166][167][168]. CM promoted by 1 followed by dihydroxylation using NaIO4 as an oxidant delivered diol products through rutheniumcatalyzed dihydroxylation.…”

Section: Stereoselective Olefin Metathesis In Synthetic Applicationsmentioning

confidence: 99%

Recent Advancements in Stereoselective Olefin Metathesis Using Ruthenium Catalysts

2017

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Olefin metathesis is a prevailing method for the construction of organic molecules. Recent advancements in olefin metathesis have focused on stereoselective transformations. Ruthenium olefin metathesis catalysts have had a particularly pronounced impact in the area of stereoselective olefin metathesis. The development of three categories of Z-selective olefin metathesis catalysts has made Z-olefins easily accessible to both laboratory and industrial chemists. Further design enhancements to asymmetric olefin metathesis catalysts have streamlined the construction of complex molecules. The understanding gained in these areas has extended to the employment of ruthenium catalysts to stereoretentive olefin metathesis, the first example of a kinetically E-selective process. These advancements, as well as synthetic applications of the newly developed catalysts, are discussed.

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Tandem ROMP−Hydrogenation with a Third-Generation Grubbs Catalyst

Cited by 103 publications

References 28 publications

Improved Syntheses of Versatile Ruthenium Hydridocarbonyl Catalysts Containing Electron‐Rich Ancillary Ligands

Improved Syntheses of Versatile Ruthenium Hydridocarbonyl Catalysts Containing Electron‐Rich Ancillary Ligands

Ring-Opening Metathesis Polymerization and Hydrogenation of Ethyl-substituted Tetracyclododecene

Recent Advancements in Stereoselective Olefin Metathesis Using Ruthenium Catalysts

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