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Ruthenium Scavenging with SiliaMetS

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Ruthenium-based catalysts are commonly used in organic synthesis, mainly in olefin metathesis reaction [ROM(P) and RCM]. Grubbs and Hoveyda-Grubbs catalysts are certainly the most popular ruthenium-based complexes in that field of applications. Complete ruthenium removal can be tedious using conventional methods.
SiliaMetS allow to reach the maximal tolerated concentration of the residual ruthenium. A ruthenium scavenging study was conducted and various parameters were investigated in order to learn more on their influence on the scavengers’ robustness as well as to establish the best experimental conditions.

Ruthenium Scavenging Results using SiliaMetS
SiliaMetS Grubbs 1st Gen. Grubbs 2nd Gen. Hoveyda-Grubbs 1st Gen. Hoveyda-Grubbs 2nd Gen.
Toluene1 DMF2 Toluene1 DMF2 Toluene1 DMF2 Toluene1 DMF2
SiliaMetS Thiol 90 % 96 % - 99 % 97 % 93 % - -
SiliaMetS Thiourea - 98 % - 96 % 97 % 98 % - -
SiliaMetS DMT 95 % 99 %2 > 99 % 99 %2 > 99 %2 98 %2 98 %2 99 %2
SiliaMetS Amine 95 % 97 % 92 % - - - - -
SiliaMetS Diamine 99 % 99 % 91 % 94 % > 99 % 98 % - 90%
SiliaMetS Triamine - 95 % - - 93 % 95 % - 95 %
SiliaMetS TAAcOH 93 % - - - - - - -
SiliaMetS TAAcONa 96 % - 96 % - 98 % - - -
Exp. Conditions: 1 8 eq. of SiliaMetS, 16 h, 80°C; 2 Only 4 eq. of SiliaMetS. Initial concentration: 500 ppm for all ruthenium-based catalysts.
Note: SiliaMetS Cysteine and Imidazole were not screen in this study (not launch at this moment). Only SiliaMetS results higher than 90% are presented in this table.

 

SiliaMetS vs Other Purification Methods

The use of SiliaMetS to remove ruthenium catalyst after ring-closing metathesis (RCM) reaction is the most effective purification method (over conventional ones). As demonstrated below, the main advantage is no product lost during the purification step.

case-study-other-purification

 

Scavenging Results for Various Purification Methods*
Scavenging Scavenger Filtration over packed bed of ...2 Flash Purification
SiliaMetS DMT1 Act. Carbon Celite Silica Manual SiliaSep Cart.
Ruthenium captation 93 % 73 % 24 % 58 % 70 % 73 %
1 Using 4 eq., 16h, 22°C. 2 Solution passed directly on a packed bed of various adsorbents, then washed with the same quantity of solvent.
*Quantitative yield obtained for each purification method (adjusted in function of the residual concentration of catalyst). No impurity generated in all cases using the different methods (determined by NMR).

 

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  1. SiliaMetS Triamine metal scavenger (R48030B)

    SiliaMetS Triamine (R48030B)

    Effective for scavenging metals such as Pb, Co, Ru and Pd. Our screening studies have shown it to be the preferred scavenger for Pb. It can also be used as a scavenger for acid chlorides, isocyanates and other electrophiles.
  2. SiliaMetS Diamine (R49030B)

    SiliaMetS Diamine (R49030B)

    SiliaMetS is a proven scavenger for metals and electrophiles. It scavenges acids, acid chlorides, anhydrides, aldehydes, isocyanates, and chloroformates. Best metal scavenger for: Cr, Pd, Pt, W & Zn. Good scavenger for: Cd, Co, Cu, Fe, Hg, Ni, Pb, Ru, Sc, Se & V.
  3. SiliaMetS Thiol (SH) (R51030B)

    SiliaMetS Thiol (SH) Metal Scavenger (R51030B)

    Our most versatile and robust metal scavenger for a variety of metals under a wide range of conditions. Best scavenger for: Ag, Hg, Os, Pd & Ru. Good scavenger for: Cu, Ir, Pb, Rh, Se & Sn.
  4. SiliaBond Amine (WAX) (R52030B)

    SiliaBond Amine (WAX) (R52030B)

    SiliaBond Amine (Si-NH2) is an effective scavenger of acid chlorides, sulfonyl chlorides, isocyanates and other electrophiles. Si-NH2 has been shown to be effective metal scavenger and catalyst for Knoevenagel reactions. SiliaBond Amine is also used in chromatography as normal phase sorbent.
  5. SiliaMetS TAAcOH nec (R69030B)

    SiliaMetS TAAcOH nec (R69030B)

    SiliaMetS TAAcOH is an effective scavenger for metals in low or zero oxidation states, which includes many of the most synthetically useful catalysts. Best scavenger for: Ca, Co, Ir, Li, Mg, Ni, Os, Ru & Sc. Good scavenger for: Cr, Cs, Fe, Pd, Rh & Sn.
  6. SiliaMetS TAAcONa nec (R69230B)

    SiliaMetS TAAcONa nec (R69230B)

    SiliaMetS TAAcONa or (or SiliaMetS Triaminetetraacetate, sodium salt) is a silica bound metal scavenger for Pd(II), Ni(II) and Cu. It is the supported version of EDTA in its sodium salt form. It is an effective scavenger for metals in higher oxidation state, 2+ or higher.
  7. SiliaMetS Thiourea (THU) (R69530B)

    SiliaMetS Thiourea (THU) (R69530B)

    SiliaMetS Thiourea (Si-THU) is a versatile metal scavenger for all forms of palladium, and is widely used in the pharmaceutical industry. Once complexed with a transition metal, it has also been reported as being an effective catalyst. Best scavenger for: Pd & Ru. Good scavenger for: Ag, Cu, Fe, Os, Rh, Sc & Sn.
  8. SiliaMetS DMT (Dimercaptotriazine) (R79030B)

    SiliaMetS DMT (Dimercaptotriazine) (R79030B)

    SiliaMetS DMT is the silica - bound equivalent of 2,4,6 - trimercaptotriazine (trithiocyanuric acid, TMT). It is a versatile metal scavenger for a variety of metals and the preferred metal scavenger for ruthenium catalysts and hindered Pd complexes. Best scavenger for: As, Ir, Ni, Os, Pd, Pt, Rh, Ru & Se. Good scavenger for: Cd, Co, Cu, Fe, Sc & Zn.

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