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AquaMet

AquaMet

Chemical name:

(4-((4-ethyl-4-methylpiperazin-1-ium-1-yl)methyl)-1,3-dimesitylimidazolidin-2-ylidene)dichloro(2-isopropoxybenzylidene)ruthenium(II) chloride

Product number: AS2038

CAS number: 1414707-08-6

Patent number: PCT/EP2013/053967

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Description

Water soluble catalyst. Substrate scope similar to classical complexes like nitro-Grela or Grubbs second generation catalyst. Soluble also in some chlorinated  organic solvents (DCM, chloroform).

Chemical properties

Chemical formula:

C39H55Cl3N4ORu

Molecular weight:

803.31 g/mol

Physical state:

powder

Color:

green

Handling information

High stability allows catalyst handling on air.

Storage information

Long-term storage (>1 week):

Store under inert gas in a cold place (recommended temp. 2 - 8 °C).

Short-term storage (<1 week):

Store under inert gas at ambient temperature.

Applications

S. Masuda, S. Tsuda, T. Yoshiya, “Ring-closing metathesis of unprotected peptides in water” Org. Biomol. Chem., 16, 9364, (2018).

 

 

J. Pastva, K. Skowerski, S. J. Czarnocki, N. Zilkova, J. Cejka, Z. Bastl, H. Balcar “Ru-Basedd Complexes with Quaternary Ammonium Tags Immobilized on Mesoporous Silica as Olefin Metathesis Catalysts” ACS Catal., 4, 3227-3236, (2014).

 

 

K. Skowerski, G. Szczepaniak, C. Wierzbicka, Ł. Gułajski, M. Bieniek, K. Grela “Highly active catalysts for olefin metathesis in water” Catal. Sci. Technol., 2(12), 2424 – 2427, (2012). 

 

Additional references

  • L. Jongkind, M. Rahimi, D. Poole III, S. J. Ton, D. E. Fogg, J. Reek “Protection of ruthenium olefin metathesis catalysts in a self-assembled resorcinarene capsule” ChemCatChem, doi:10.1002/cctc.20200011, (2020).
  • S. Planer, A. Jana, K. Grela “Ethyl lactate: A green solvent for olefin metathesis” ChemSusChem, doi:10.1002/cssc.201901735, (2019).

  • B. O. Ozturk, S. K. Sehitoglu “Pyrene substituted amphiphilic ROMP polymers as nano-sized fluorescence sensors for detection of TNT in water” Polymer, 183, 121868, (2019).

  • B. O. Ozturk, D. Gurcu, S. K. Sehitoglu “Carbocyclic acid addition to terminal alkynes utilizing ammonium tagged Hoveyda-Grubbs catalyst supported on magnetically separable core/shell silica: A highly reusable and air compatible catalytic system” J. Organomet. Chem., 883, 11-16, (2019).

  • G. Szczepaniak, W. Nogaś, J. Piątkowski, A. Ruszczyńska, E. Bulska, K. Grela “Purification Protocol for the Removal of Ruthenium Impurities from Olefin Metathesis Reaction Products Using an Isocyanide Scavenger” Org. Process Res. Dev., 23, 836-844, (2019).

  • Ł. Gułajski, A. Tracz, K. Urbaniak, S. J. Czarnocki, M. Bieniek, T. K. Olszewski “Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation” Beilstein J. Org. Chem., 15, 160-166, (2019).

  • D. B. Wright, M. A. Touve, M. P. Thompson, N. C. Gianneschi “Aqueous-Phase Ring-Opening Metathesis Polymerization-Induced Self-Assembly” ACS Macro Lett., 7, 401 – 405, (2018).

  • G. Szczepaniak, A. Ruszczyńska, K. Kosiński, E. Bulska, K. Grela “Highly efficient and time economical purification of olefin metathesis products from metal residues using an isocyanide scavenger” Green Chemistry, 20(6), 1280-1289, (2018).

  • A. Chołuj, A. Zieliński, K. Grela, M. J. Chmielewski “Metathesis@MOF: Simple and Robust Immobilization of Metathesis Catalysts inside (Al)MIL-101-NH2” ACS Catal., 6, 6343-6349, (2016).

  • H. Balcar, N. Zilkova, M. Kubu, M. Mazur, Z. Bastl, J. Cejka “Ru complexes of Hoveyda-Grubbs type immobilized on lamellar zeolites: activity in olefin metathesis reations” Beilstein J. Org. Chem., 11, 2087-2096, (2015).

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