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A Closer Look at Our Newest Metathesis Catalysts and Metal Scavengers

Strem has Added Two New Core Catalysts and a Metal Scavenger from Apeiron

We have recently introduced two new metathesis catalysts and a metal scavenger from Apeiron Synthesis to add to our existing collaborative product line.

44-0760 

HeatMet (44-0760), a catalyst for ROMP, is a highly efficient latent catalyst, requiring thermal activation to initiate catalytic activity.  Its characteristics are especially suitable to mold polymerization of reactive monomers such as dicyclopentadiene (DCPD).  The catalyst is soluble in toluene and dichloromethane.[i]

44-0759

The use of metal and metal organic catalysts to perform synthesis often requires consideration for the removal of the metal from the desired product. This is particularly true for pharmaceutical manufacturing where the amount of trace-metals in the drug product must be in low ppm ranges. [ii]

As part of Apeiron’s approach to address this need for removal of trace-metals from the product, FixCat (44-0759) was developed.  A Hoveyda-type catalyst, FixCat’s structure was optimized to serve as a versatile and very stable catalyst, easily immobilized on solid supports. In a mesoporous silica version (SBA-15 14-8820), it showed exceptional efficiency in promoting ring-closing and cross-metathesis reactions, in both batch and continuous flow setups.[iii] The solid supported catalyst can be easily removed by filtration with residual ruthenium below 10 ppm.  Recovered catalysts can be reused several times with no loss of activity.

FixCat can also be employed as a homogeneous catalyst. It is soluble in water, dichloromethane and alcohols.

07-2203

Another approach to metal removal is Apeiron Synthesis’ unique metal scavenger. SnatchCat (07-2203) represents a universal tool for metal removal with a proven efficiency for ruthenium and palladium. The product is an immediate metathesis reaction quencher, allowing reduced metal content below 10ppm after 20 min scavenging time and a simple workup by silica gel filtration.  Typically, only 4 equivalents are required with respect to the catalyst. Compatible with a broad range of functional groups and solvents, SnatchCat is stable, nontoxic, non-volatile and odor-free.[iv]

These three products have been added to the Apeiron Ruthenium Metathesis Catalyst Kit (96-0400).

These catalysts are sold in collaboration with Apeiron Synthesis: www.apeiron-synthesis.com

 

References:

[i] S. J. Czarnocki, I. Czelusniak, K. Skowerski, T. K. Olszewski, K. Grela. Aza Analogues of Hoveyda-type Catalyst Containing an Ester Group on the Chelating Nitrogen Atom: Synthesis, Structural and Application Studies. Manuscript in preparation.

[ii]Thayer, A. Removing Impurities. Chem. Eng. News, 2005, 83 (36), 55-58

[iii] Pastva, J.; Skowerski, K.; Czarnocki, S. J.; Žilková; N.;  Čejka, J.; Bastl, Z.; Balcar, H. ACS Catal., 2014, 4 (9), 3227–3236; Skowerski, K.; Pastva, J.; Czarnocki, S.J.; Janoscova, J. Org. Process Res. Dev., 201519 (7), 872–877

[iv] G. Szczepaniak, K. Urbaniak, C. Wierzbicka, K. Kosiński, K. Skowerski, K. Grela, ChemSusChem 20158, 4139.

 

Visit the links below to view additional details on our website:

Apeiron Metathesis Catalysts

The Strem Chemiker - Vol. XXVIII No. 1 - June, 2015 (Featured Article: Olefin Metathesis: New Catalysts, New Solutions for Process Chemistry)

 

Products mentioned in this blog:

07-2203: 1,4-Bis(2-isocyanopropyl)piperazine (SnatchCat Metal Scavenger)  [ 51641-96-4]

14-8820: SBA-15 Molecular Sieve  [7631-86-9]

44-0759: (1,3-Bis(2,6-diisopropylphenyl)-4-((4-ethyl-4-methylpiperzain-1-ium-1-yl)methyl)imidazolidin-2-ylidene)(2-isopropoxybenzylidene)ruthenium(II) chloride dihydrate FixCat  [1799947-97-9]

44-0760: Dichloro(1,3-dimesitylimidazolidin-2-ylidene){2-[(ethoxy-2-oxoethylidene)amino]benzylidene} ruthenium(II) HeatMet

96-0400: Apeiron Ruthenium Metathesis Catalyst Kit

 

 

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