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Chemoselective Reduction Catalysts
Osmium-Activated Carbon and Palladium Catalyst Series


In catalytic reduction, palladium-carbon (Pd/C), a heterogeneous catalyst, is widely used since it can effectively reduce various functional groups under mild neutral conditions. By Pd/C, however, chemoselectivity or regioselectivity cannot be achieved due to the strong reducing ability. To solve these problems, Wako provides fi xed catalysts which have chemoselectivity by using ethylenediamine (abbreviated product name [Pd/C (en)] 1)), fi broin (abbreviated product name [Pd/Fib] 2)), or polyethyleneimine (abbreviated product name [Pd/PEI] 3)) as a catalyst poison.
In addition to the above, osmium-activated carbon, a complex of osmium with activated carbon, shows different selectivity (reduction of aromatic nitro groups prior to olefi ns) from the existing palladium catalysts.


INDEX

  1. Osmium-Activated Carbon [Os/C]
  2. Palladium Catalyst Series
  3. ChemoselectiveReduction Catalyst Set
  4. Product List

1.Osmium-Activated Carbon [Os/C]

Aromatic amine compounds are gaining attention for their effectiveness as materials for polymers and as intermediates for pharmaceutical formulations. Such production processes usually involve the reduction of Aromatic nitro compounds with a stoichiometrically appropriate amount of activated iron powder. Consequently, the inconvenience of removing iron following reduction has been an issue complicating the use of aromatic nitro compounds for industrial purposes. Osmium-activated carbon (Os/C) enables selective hydrogenation of the nitro moiety without affecting the other various functional groups in aromatic nitro compounds t hat can be reduced. This unique property of Os/C is highly advantageous in creating new synthesis pathways.

Features
  • It selectively reduces aromatic nitro groups.
  • Less combustible.
  • New type catalyst which is not a toxic and volatile osmium tetroxide.


Reaction example


Example of use
Add 1 g nitrostilbene, 10 mL methanol, 100 mg 5% Os/C and 2 mL hydrazine hydrate to a Florence flask. React the mixture by agitating for 4 h at 60°C. Afterwards, filter out the 5% Os/C from the solution while washing with water and ethyl acetate. Perform extraction on the filtrate twice with ethyl acetate and then wash along with the organic phase with saturated NaCl brine. After drying the organic phase with anhydrous magnesium sulfate, filter and vacuum-concentrate. Refine the crude product using silica gel column chromatography.

Product Name Abbr. Grade Pkg. size Wako Cat. No.
Osmium-Activated Carbon(Os 3.5-6.5%) Os/C for Organic Synthesis 1 g 151-02881
5 g 157-02883
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2. Palladium Catalyst Series

We offer immobilized catalysts with ethylenediamine, fibroin or polyethyleneimine as catalyst poisons that enable selective catalytic reduction of targeted functional groups.

Features
  • Enables selective reduction
  • Has low combustibility



2-1. Palladium-Activated Carbon Ethylenediamine Complex [5% Pd/C(en)]

Use of 5% Pd/C(en) prevents the reduction of protective moieties including benzyl ethers, benzyloxycarbonyl (Cbz) groups on aliphatic amines, O-tert-butyldimethylsilyl (O-TBDMS) grouvvvvvvvvps, epoxides and benzyl alcohols, while at the same time conveniently enabling the selective catalytic reduction of olefins, azides, nitro groups, benzyl esters and aromatic halogens.

Reaction example
  1) Selective reduction in the presence of a benzyl ether group2)

  2) Selective reduction in the presence of Cbz2)


Product Name Grade Pkg. size Wako Cat. No.
Palladium-Activated Carbon Ethylenediamine Complex (Pd 3.5 ~ 6.5 %) for Organic Synthesis 1 g 163-21441
5 g 169-21443
25 g 161-21442
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QUOTATION REQUEST for Chemoselective Reduction Catalysts


2-2. 10% Pd/C(en)

10% Pd/C(en) can be used for regioselective reduction of 1,2-epoxides, selective acetoxy group elimination reactions, and selective reduction in the presence of O-tert-butyldimethylsilyl (O-TBDMS) groups

Reaction example
1) Regioselective reduction of a 1,2 epoxide

Product Name Grade Pkg. size Wako Cat. No.
Palladium-Activated Carbon Ethylenediamine Complex
(Pd8.5~11.5%)
for Organic Synthesis 1 g 167-23301
5 g 163-23303
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2-3. Palladium-Fibroin [Pd/Fib]

Made by depositing 2.5% Pd deposited onto silk fibroin, this catalyst provides stronger protection against the breakdown of unstable functional groups during hydrogenation reactions than Pd/C(en). Use of Pd/Fib prevents the reduction of protective moieties including benzyl ester, benzyloxycarbonyl (Cbz) groups on aromatic amines, aromatic halogens and aromatic carbonyl groups, while at the same time conveniently enabling the selective catalytic reduction of olefins, azides, nitro groups.

Reaction example

Product Name Abbr. Grade Pkg. size Wako Cat. No.
Palladium-Fibroin Pd/Fib for Organic Synthesis 1 g 167-22181
5 g 163-22183


2-4. Palladium-Polyethyleneimine [Pd/PEI]

In general, selective partial hydrogenation of alkenes to produce alkanes is extremely difficult and requires the use of a Lindlar catalyst with lead as a catalyst poison. However, not only is this method environmentally unfriendly, it cannot be applied to converted alkenes. This catalyst was developed to resolve such issues by employing polyethyleneimine polymer, which contains many basic amines, as a strong catalyst poison and supporter for palladium, and enables the selective reduction of double bonds to synthesize desired alkanes.

Product Name Abbr. Grade Wako Cat. No. Pkg. size
Palladium-Polyethyleneimine Pd/PEI for Organic Synthesis 1 g 161-22221
5 g 167-22223
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QUOTATION REQUEST for Chemoselective Reduction Catalysts

2-5. References

  1. H.Sajiki, K.Hattori, K.Hirota, J.Org.Chem., 63,7990(1998).
  2. H.Sajiki, T.Ikawa, H.Yamada, K.Tsubouchi, K.Hirota. Tetrahedron Lett., 44,171(2003).
  3. H.Sajiki, S.Mori, T.Ohkubo, T.Ikawa, A.Kume, T.Maegawa, Y.Monguchi, Chem.Eur.J., 14,5109(2008).
3. ChemoselectiveReduction Catalyst Set

We supply 5 selective reduction catalysts with functional grpu@ selectivity such as Palladium-Activated Carbon Ethylenediamine、Palladium-Fibroin、 Palladium-Polyethyleneimine and Osmium-Activated Carbon in a kit. You can choose the catalyst of interest by comparing these catalysts with various activities.

Leaflet (358KB/2p)

Reaction example


Product Name Pkg. size Wako Cat. No.
Chemoselective Reduction Calalysts Set 1 set 032-21041
<Kit Contents> <Pkg. size> <Abbreviation>
  • Palladium-Activated Carbon Ethylenediamine Complex (Pd 3.5-6.5%)
  • 1 g 5% Pd/C(en)
  • Palladium-Activated Carbon Ethylenediamine Complex (Pd 8.5-11.5%)
  • 1 g 10% Pd/C(en)
  • Palladium-Fibroin
  • 1 g Pd/Fib
  • Palladium-Polyethyleneimine
  • 1 g Pd/PEI
  • Osmium-Activated Carbon(Os 3.5-6.5%)
  • 1 g Os/C
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    4. Product List

    # Product Name Abbr. Pkg. size Wako Cat. No.
    1 Osmium-Activated Carbon (Os 3.5-6.5%) Os/C 1 g 151-02881
    5 g 157-02883
    2-1 Palladium-Activated Carbon Ethylenediamine Complex (Pd 3.5~6.5 %)   1 g 163-21441
    5 g 169-21443
    25 g 161-21442
    2-2 Palladium-Activated Carbon Ethylenediamine Complex (Pd8.5~11.5%)   1 g 167-23301
    5 g 163-23301
    2-3 Palladium-Fibroin Pd/Fib 1 g 167-22181
    5 g 163-22183
    2-4 Palladium-Polyethyleneimine Pd/PEI 1 g 161-22221
    5 g 167-22223
    3 Chemoselective Reduction Calalysts Set 1 set 032-21041
    Kit Contents (1 g each)
  • Palladium-Activated Carbon Ethylenediamine Complex (Pd 3.5-6.5%) [5% Pd/C(en)]
  • Palladium-Activated Carbon Ethylenediamine Complex (Pd 8.5-11.5%) [10% Pd/C(en)]
  • Palladium-Fibroin [Pd/Fib]
  • Palladium-Polyethyleneimine [Pd/PEI]
  • Osmium-Activated Carbon(Os 3.5-6.5%) [Os/C]
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    QUOTATION REQUEST for Chemoselective Reduction Catalysts

    Note

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