Chemical Synthesis

EnCat™ & Other Catalysts

Partnering with Reaxa, Sigma-Aldrich offers a variety of transition metal-based encapsulated catalysts for applications in areas such as Suzuki, Stille, and Heck couplings, carbonylations, hydrogenation, hydrogenolysis, and dihydroxylation.

Coupling Chemistry

Pd(II) EnCat™

Pd(II) EnCat™ covers a versatile range of immobilized palladium acetate catalysts with or without activating ligands contained in a robust, porous polyurea matrix which allow easier, faster and cleaner reaction processes to be developed. The recyclable catalysts have demonstrated superb activity in cross-couplings, Heck couplings, and carbonylations.

Cleaner products Typically less than 10 ppm Pd in crude product
Cleaner waste streams Reduced metal losses in Pd EnCat™ processes
Fast, efficient processes EnCat™ beads filter easily
No plant contamination Metal and ligands are trapped within the beads
Improved processes High activity in many types of coupling reactions
Process intensification Can be used in batch and flow processes

 
Technical Information for Download (PDF format):

1) Pd(0) and Pd(II) EnCat™ Presentation (2.8 MB PDF)
2) Pd(II) EnCat™ Technical Flier (485KB PDF)
3) Pd(II) EnCat™ User Guide (72 KB PDF)
4) ChemFiles 2007 Supplement 1: Encapsulated Catalysts and Metal Scavengers (624 KB PDF)

Cheminar™ 1.1: Pd EnCat™ Technology (click here to view)

Product #  Product Name Co-encapsulated Ligand Description Add to Cart
644714 Pd(II) EnCat™ 30 none Extent of labeling: 0.4 mmol/g Pd loading
644722 Pd(II) EnCat™ 40 none Extent of labeling: 0.4 mmol/g Pd loading
644706 Pd(II) EnCat™ TPP30 PPh3 Extent of labeling: 0.4 mmol/g Pd loading, Pd 1.0, TPP 0.8
644692 Pd(II) EnCat™ TOTP30 P(o-tolyl)3 Extent of labeling: 0.4 mmol/g Pd loading, Pd 1.0, TOTP 0.5
658693  Pd(II) EnCat™ BINAP30 rac-BINAP Extent of labeling: 0.39 mmol/g Pd loading, Pd 1.0, BINAP 0.25
666335 Pd(II) EnCat™ Kit I Contains 1 g units of: 644692, 644706, 644714, 644722, and 658693


References:
1) Ladlow, M et al. Org. Biomol. Chem. 2003, 1, 2419.
2) Ley, S. V. et al. Org. Biomol. Chem. 2004, 2, 611.
3) Ley, S. V. et al. Chem. Commun. 2005, 2175.
4) Pilotti, P. et al. Pharm. Disc. 2005, 5(8), 32.
5) Nájera, C. et al. Tetrahedron 2005, 61, 12168.
6) Ley, S. V. Chem. Eur. J. 2006, 12, 4407.
7) Yamamoto, Y. et al. Synlett 2006, 1027.
8) Ley, S. V. et al. Chem. Commun. 2002, 1132.
9) Ley, S. V. et al. Chem. Commun. 2002, 1134.
10) Ley, S. V. et al. Synlett 2002, 1843.
11) Pears, D. A. et al. Aldrichimica Acta 2005, 38, 23.
12) Leeke, G. A. et al. Org. Process Res. Dev. 2007, 11, 144.
13) Ley, S. V. et al. Synlett 2007, 1251.

LaPCatTM

The LaPCatTM kit is an exclusive collection of six palladium and/or copper containing perovskite heterogeneous catalysts for use in a wide range of organic reactions. LaPCatTM catalysts demonstrate superb catalytic activity in many coupling reactions with a wide variety of substrates.


Catalyst Formulation Surface Area (m2/g) Particle Size (μm) Reactions
FP2 LaFe0.95Pd0.05O3 5.5 41.1 Suzuki
FP8 LaFe0.80Pd0.20O3 5.7 3.3 Suzuki
CoP LaFe0.57Co0.38Pd0.05O3 3.4 4.0 Suzuki, Heck, Sonogashira
CuP LaFe0.57Cu0.38Pd0.05O3 12 3.7 Suzuki, Sonogashira, Ullmann
CoCu La0.9Ce0.1Co0.60Cu0.40O3 7.9 5.4 Ullmann
YBCu YBa2Cu3O7 0.3 10.6 Ullmann

As shown in the table above, the various LaPCatTM catalysts have broad application in several important classes of carbon-carbon bond forming reactions.

Cleaner products Typically ≤10 ppm of metal contamination in crude product
Cleaner waste streams Reduced metal losses in LaPCat™ processes
Fast, efficient processes Equivalent or better than homogeneous catalysts
Improved processes Very low catalyst loadings achieved
Improved cost effectiveness LaPCat™ catalysts may be reused

Technical Information for Download (PDF format):

1) LaPCatTM Presentation (1.3 MB PDF)
2) LaPCatTM Technical Flier (365 KB PDF)
3) LaPCatTM User Guide (287 KB PDF)
4) ChemFiles 2007 Supplement 1: Encapsulated Catalysts and Metal Scavengers (624 KB PDF)

 

Product #  Product Name Description Add to Cart
674052 LaPCat™ Perovskite Catalyst Kit I Six 100 mg samples of LaPCat™ catalysts: FP2, FP8, CoP, CuP, CoCu, and YBCu



Hydrogenation

Pd(0) EnCat™ 30NP

Pd(0) EnCat™ 30NP is a versatile polymer encapsulated nanoparticulate Pd(0) hydrogenation and transfer hydrogenation catalyst with high chemoselectivity and improved safety profile allowing easier, faster and cleaner processes to be developed. Reaxa’s controlled manufacturing process produces regular palladium(0) nanoparticles stabilized by the polymer matrix within the EnCat™ beads, ensuring that the catalyst performance is extremely reproducible from batch to batch (c.f. palladium on carbon).

Cleaner products Typically <1 ppm Pd in crude product
Cleaner waste streams Reduced metal losses in EnCat™ processes
Fast, efficient processes EnCat™ beads filter easily and can be recycled
No plant contamination Pd metal is trapped within the beads
High selectivity In hydrogenation and transfer hydrogenation reactions
Improved safety profile Less pyrophoric compared with Pd/C catalysts
Process intensification Can be used in batch and flow processes

Technical Information for Download (PDF format):

1) Pd(0) and Pd(II) EnCat™ Presentation (2.8 MB PDF)
2) Pd(0) EnCat™ 30NP Technical Flier (518 KB PDF)
3) Pd(0) EnCat™ 30NP User Guide (340 KB PDF)
4) Pd(0) EnCat™ 30NP Debenzylation Guide (159 KB PDF)
5) ChemFiles 2007 Supplement 1: Encapsulated Catalysts and Metal Scavengers (624 KB PDF)

 

Cheminar™ 1.1: Pd EnCat™ Technology (click here to view)

 

Product #  Product Name Description Add to Cart
653667 Pd(0) EnCat™ 30NP nanoparticles, extent of labeling: 0.4 mmol/g Pd loading


References:
1) Ley, S. V. et al. Chem. Comm. 2003, 678.
2) Ley, S. V. et al. Beil. J. Org. Chem. 2006, 2, 15.
3) Ley, S. V. et al. Org. Lett. 2003, 5, 4665.
4) Ley, S. V. et al. Org. Biomol. Chem. 2004, 2, 160.
5) Ley, S. V. et al. Chem. Commun. 2002, 1132.
6) Pears, D. A. et al. Aldrichimica Acta 2005, 38, 23.
7) Quai, M. et al. Tetrahedron Lett. 2007, 48, 1241.

Pt(0) EnCat™ 40

Pt(0) EnCat™ 40 is a versatile hydrogenation catalyst demonstrating high chemoselectivity and improved safety profile over platinum on carbon allowing easier, faster and cleaner processes to be developed. Isolating the active platinum within the polymer matrix has produced an easily-handled and safer alternative to Pt/C. The catalyst is particularly effective for hydrogenation of nitro groups and reductive aminations in the presence of halogens.
 

Cleaner products Very low levels of Pt in crude product
Cleaner waste streams Reduced metal losses in EnCat™ process (typically <0.005% Pt loss)
Fast, efficient processes EnCat™ beads filter easily
No plant contamination Pt metal remains entrapped within the beads
High selectivity In hydrogenation reactions
Process intensification Can be used in batch and flow processes
Improved safety profile Initial tests show no tendency of activated catalyst to ignite on exposure to air


Technical Information for Download (PDF format):

1) Pt(0) EnCat™ 40 Presentation (323 KB PDF)
2) Pt(0) EnCat™ 40 Technical Flier (43 KB PDF)
3) Pt(0) EnCat™ 40 User Guide (43 KB PDF)
4) ChemFiles 2007 Supplement 1: Encapsulated Catalysts and Metal Scavengers (624 KB PDF)

Product #  Product Name Description Add to Cart
681504 Pt(0) EnCat™ 40 Wet, encapsulated nanoparticles, extent of labeling: 0.12 mmol/g Pt loading (dry basis)

Dihydroxylation

Os EnCat™ 40

Osmium tetroxide (OsO4)is known to be one of the most reliable and effective catalysts for oxidative cleavage and dihydroxylation of olefins. However, it is very toxic, volatile and expensive, thus limits its usefulness at large-scale. Os EnCat™ 40 effectively immobilizes and stabilizes osmium tetroxide to produce a safer and easier-to-use catalyst for application in oxidation chemistry.

In the above picture, a vial containing Os EnCat™ 40 placed in the presence of corn oil is unchanged after several months, whereas an equivalent sample of volatile osmium tetroxide quickly reacts to produce black decomposition products, indicating the stability of the encapsulated OsO4.
 

Cleaner products Typically less than 100 ppm Os in crude product
Easier storage, transport and use Low residual OsO4 vapor over Os EnCat™ product
Faster, efficient processes Resin beads filter easily
High selectivity Can be used for asymmetric dihydroxylation
Reduced plant contamination OsO4 is trapped in the beads
Improved cost effectiveness Os EnCat™ 40 may be reused in repeat reaction cycles
Process intensification Can be used in batch and flow processes

Technical Information for Download (PDF format):

1) Os EnCat™ 40 Technical Flier (73 KB PDF)
2) Os EnCat™ 40 User Guide (111 KB PDF)
3) ChemFiles 2007 Supplement 1: Encapsulated Catalysts and Metal Scavengers (624 KB PDF)

Product #  Product Name Description Add to Cart
658685 Os EnCat™ 40 Extent of labeling: 0.3 mmol/g Os loading

References:
1) Ley, S. V. et al. Org. Lett. 2003, 5, 185.
2) Borhan, B. et al. Tetrahedron Lett. 2006, 47, 3797.
3) Ley, S. V. et al. Org. Lett. 2003, 5, 185.
4) Ley, S. V. et al. Org. Biomol. Chem. 2003, 1, 3957.