tBuXPhos Pd G3

• CAS: 1447963-75-8
• Catalog Number: ACM1447963758
• Category: Main Products
• Molecular Weight: 795.40
• Molecular Formula: C42H59NO3PPdS
• Synonyms: TBuXPhos-Pd-G3
• Appearance: Yellow solid
• Application: Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media.

Case Study

tBuXPhos Pd G3 Catalytic Systems for Buchwald-Hartwig Amination

Gevorgyan, Ashot, et al. Organometallics, 2021, 41(14), 1777-1785.

This study explored the capabilities and limitations of Buchwald-Hartwig amination using lipids as solvents. It identified the most effective catalytic systems for unactivated aryl halides and sulfonates, with the highest yields produced by systems based on either BrettPhos Pd G3/BrettPhos or tBuXPhos Pd G3/tBuXPhos.
· Experimental Procedures for Buchwald-Hartwig Amination
Inside an argon-filled glovebox, a dried 10 mL flask was sequentially filled with tBuXPhos Pd G3 (2 mol %), tBuXPhos (2 mol %), K2CO3 (2 equivalents), and the appropriate nucleophile (1.5 equivalents). The flask was sealed with a rubber septum, removed from the glovebox, and connected to an argon balloon. Next, 3 mL of rapeseed oil and the corresponding aryl halide or sulfonate ester (1 equivalent, 0.869-0.948 mmol) were added. The argon balloon was then detached, and the mixture was stirred at 110 °C for 24 hours. After the reaction, the mixture was allowed to cool, and the product was isolated.
· Catalytic Systems Based on tBuXPhos Pd G3
Using these catalysts, good yields were obtained for various nucleophiles, including heterocycles like indole and pyrrole (3g,h; 65-91%). Satisfactory yields were also seen for secondary anilines (3d,e; 55-62%), primary amines (3f; 50%), and phenols (3i; 56%). The screening of aryl halides and sulfonates confirmed that this methodology is highly effective for generating secondary anilines in quantitative yields. Excellent results were achieved with both electron-rich (3j-m; 96-99%) and electron-deficient (3n,o; 97-99%) aryl bromides, chlorides, and aryl triflates. Moderate yields were observed in Buchwald-Hartwig amination only for electron-rich and labile heterocycles (3p,q; 49-71%), such as 3-bromothiophene and 2-bromobenzothiophene.

tBuXPhos Pd G3 for Validation of Catalytic Fluorescence Determination of Trace Pd in Ibuprofen

DaRos, Judey T., et al. The Journal of Organic Chemistry, 2024, 89(11), 8005-8010.

To verify whether the quiescent Pd species in the API can catalyze the O-deallylation of resorufin allyl ether (RAE) under analytical conditions, the Buchwald precatalyst tBuXPhos-Pd-G3 and PEPPSI-IPr were selected as model reagents. The results showed that trace Pd species in the API may not need to be catalytically active because NaBH4 and TFP activate them in the analytical solution. NaBH4 is essential for robust Pd detection using this fluorescence method.
In addition, to determine the sensitivity of the fluorescence method, ibuprofen samples containing 80, 20, 5, and 0.2 ppb Pd were prepared by adding known amounts of tBuXPhos-Pd-G3 to ibuprofen solutions and then evaporating the solvent. 80 ppb Pd in ibuprofen could be semi-quantified with an error of 21%, while ≤20 ppb Pd could not be reliably quantified. Compared with conventional ICP-MS analysis, the current fluorescence method has higher throughput and lower cost for semiquantitative analysis of the same or lower concentrations of palladium in ibuprofen.

Custom Q&A

What is the PubChem CID of tBuXPhos Pd G3?

The PubChem CID of tBuXPhos Pd G3 is 90645613.

What is the molecular formula of tBuXPhos Pd G3?

The molecular formula of tBuXPhos Pd G3 is C42H59NO3PPdS.

What is the molecular weight of tBuXPhos Pd G3?

The molecular weight of tBuXPhos Pd G3 is 795.4 g/mol.

What are the synonyms of tBuXPhos Pd G3?

The synonyms of tBuXPhos Pd G3 are 1447963-75-8, TBUXPHOS PD G3, tBuXPhos-Pd-G3, Methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II) ditert-butyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane, methanesulfonic acid, palladium, and 2-phenylaniline.

When was tBuXPhos Pd G3 created?

tBuXPhos Pd G3 was created on March 1, 2015.

When was tBuXPhos Pd G3 last modified?

tBuXPhos Pd G3 was last modified on December 30, 2023.

What is the IUPAC name of tBuXPhos Pd G3?

The IUPAC name of tBuXPhos Pd G3 is ditert-butyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;methanesulfonic acid;palladium;2-phenylaniline.

What is the InChIKey of tBuXPhos Pd G3?

The InChIKey of tBuXPhos Pd G3 is IKNBBVYTGIKLPA-UHFFFAOYSA-N.

What is the CAS number of tBuXPhos Pd G3?

The CAS number of tBuXPhos Pd G3 is 1447963-75-8.

How many hydrogen bond donor counts does tBuXPhos Pd G3 have?

tBuXPhos Pd G3 has 2 hydrogen bond donor counts.

What is the full name of the compound with PubChem CID 90645613?

ditert-butyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;methanesulfonic acid;palladium;2-phenylaniline.

What is the chemical formula of the compound with PubChem CID 90645613?

C42H59NO3PPdS.

What is the molecular weight of the compound with PubChem CID 90645613?

795.4 g/mol.

What are the synonyms for the compound with PubChem CID 90645613?

1447963-75-8, TBUXPHOS PD G3, tBuXPhos-Pd-G3, Methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II) ditert-butyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;methanesulfonic acid;palladium;2-phenylaniline.

What is the IUPAC name of the compound with PubChem CID 90645613?

ditert-butyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;methanesulfonic acid;palladium;2-phenylaniline.

What is the InChIKey of the compound with PubChem CID 90645613?

IKNBBVYTGIKLPA-UHFFFAOYSA-N.

How many hydrogen bond donor counts does the compound with PubChem CID 90645613 have?

2.

How many rotatable bond counts does the compound with PubChem CID 90645613 have?

8.

How many covalently-bonded unit counts does the compound with PubChem CID 90645613 have?

4.