Pd/C

(Palladium on Carbon)

General Information:

Structure:

Pd/C

CAS Number: 7440-05-3 (CAS of palladium)

Molecular Weight: 106.42 g/mol (MW of palladium)

Appearance: Black powder

Palladium on carbon (Pd/C) is a common catalyst for hydrogenation and/or hydrogenolysis of various functional groups. It is typically purchased as a black powder which is 5% or 10% palladium (by wt%) adsorbed on carbon. The reagent is normally purchased dry or as a solid which is 50% wet with water. The 50% wet with water reagent is the safer to handle option.

Common Uses:

Catalyst for the reduction of alkenes to alkanes

Procedure excerpt:

To a solution of the SM (290 mg, 0.506 mmol) in EtOH (15 mL) was added 10% Pd/C (30 mg). The system was degassed three times (vacuum/N2), then reacted under H2 . . .

[full procedure]

Catalyst for the reduction of alkynes to alkanes

Procedure excerpt:

A mixture of the SM (80 mg, 0.23 mmol) and Pd/C (8 mg) in MeOH (5 mL) was stirred under H2 at RT for 16 h. The reaction mixture was filtered, concentrated, and purified . . .

[full procedure]

Catalyst for the reduction of nitro groups to amines

Procedure excerpt:

The SM (2.93 g, 9.18 mmol) was dissolved in EtOAc and treated with 10% Pd/C (970 mg). The reaction mixture was stirred under H2 (1 atm, balloon) overnight. . . .

[full procedure]

Catalyst for the reduction of nitriles to amines

Procedure excerpt:

A mixture of the SM (45 mg, 0.12 mmol) and Pd/C (5 mg) in 4:1 THF/NH4OH (2.5 mL) was stirred under H2 at RT for 1 h. The reaction mixture was filtered, concentrated . . .

[full procedure]

Catalyst for benzyl deprotection

Procedure excerpt:

To the SM (1.12 g, 4.14 mmol) in a Parr shaker flask was added EtOH (40 mL). The solution was purged with N2 and 10% Pd/C (0.30 g) was added. The reaction was . . .

[full procedure]

Catalyst for Cbz deprotection

Procedure excerpt:

To a solution of the SM (7.5 g, 23 mmol) in MeOH (300 mL) was added 10% Pd/C (2 g). The reaction mixture was hydrogenated in a Parr apparatus at RT . . .

[full procedure]

Safety:

Palladium on carbon (Pd/C) is pyrophoric and should be handled and disposed of according to standard protocols.

References:

1) Patent Reference: WO2016001341, page 125, (9.1 MB)

2) Patent Reference: WO2016011390, page 185, (20.2 MB)

3) Patent Reference: WO2016012477, page 153, (8.1 MB)

4) Patent Reference: WO2016011390, page 152, (20.2 MB)

5) Patent Reference: WO2012069948, page 53, (3.9 MB)

6) Patent Reference: WO2014177977, page 86, (6.0 MB)

7) Wikipedia: Palladium on carbon (link)

8) www.sigmaaldrich.com – Palladium on Carbon (link)

9) Burke, S. D.; Danheiser, R. L.; Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents