BrettPhos Pd G4 Chemical Properties

storage temp. 

2-8°C, protect from light, stored under nitrogen

form 

Powder

color 

off-white to beige

InChI

InChI=1S/2C35H53O5PS.C13H12N.CH4.Pd/c2*1-22(2)25-19-28(23(3)4)32(29(20-25)24(5)6)33-30(39-7)21-31(42(36,37)38)34(40-8)35(33)41(26-15-11-9-12-16-26)27-17-13-10-14-18-27;1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11;;/h2*19-24,26-27H,9-18H2,1-8H3,(H,36,37,38);2-7,9-10,14H,1H3;1H4;/q;;;;+1/p-2

InChIKey

ZTBOMOZSCNBFNQ-UHFFFAOYSA-L

SMILES

C1(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)=C(OC)C=C(S([O-])(=O)=O)C(OC)=C1P(C1CCCCC1)C1CCCCC1.C1(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)=C(OC)C=C(S([O-])(=O)=O)C(OC)=C1P(C1CCCCC1)C1CCCCC1.[Pd+]C1=CC=CC=C1C1=CC=CC=C1NC.C

SMILES

CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C(OC)=CC=C2OC.CNC5=C(C6=C([Pd]OS(C)(=O)=O)C=CC=C6)C=CC=C5

Safety Information

WGK Germany 

WGK 3

HS Code 

2843909000

Storage Class

11 - Combustible Solids

BrettPhos Pd G4 Usage And Synthesis

Reactions

Catalyst used for the N-arylation of amines.

Uses

• High Throughput Experimentation in Pharmaceutical Process Chemistry: This study evaluates the efficacy of BrettPhos Pd G4 in a ring closure reaction, emphasizing its selectivity and yield, which supports its potential utility in pharmaceutical synthesis (Solazzo, 2022).
• Synthesis and characterization of fluorescent amino acid dimethylaminoacridonylalanine: Research detailing the use of various Buchwald precatalysts including BrettPhos Pd G4. The study explores the synthesis of a fluorescent amino acid, highlighting the specific conditions where BrettPhos Pd G4 provided notable benefits over other catalysts (Jones et al., 2021).

General Description

BrettPhos Pd G4 is an N-substituted 2-aminobiphenylpalladium methanesulfonate precatalyst. It is a fourth generation (G4) Buchwald precatalyst that is similar to the third generation (G3) precatalysts except that the amino group on the biphenyl backbone is methylated. This modification helps to prevent the limitations of using the third generation precatalysts. It is air, moisture and thermally-stable and shows good solubility in common organic solvents. BrettPhos Pd G4 is highly useful in cross-coupling reactions. Some of its excellent features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Cross Couplings

BrettPhos Pd G4(1599466-83-7)Related Product Information

• Methanesulfonato(triphenylphosphine)(2'-amino-1,1'-biphenyl-2-yl)palladium(II) (PPH3 PD G3)
• BrettPhos Pd G3
• RuPhos Pd G1 Methyl t--Butyl Ether Adduct
• BrettPhosPalladacycle
• Palladacycle Gen. 3
• t-BuXphos Palladacycle Gen. 4
• RuPhos Palladacycle Gen. 4
• t-BuBrettPhos Palladacycle Gen. 3
• SPhos Pd G3
• SPhos Pd G1, Methyl t-Butyl Ether Adduct
• RuPhos Pd G2
• tBuXPhos Pd G1
• XPhos Pd G1
• RuPhos Pd G3
• Bis(diphenylphosphinophenyl)ether palladium (II) dichloride
• Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)
• XPhos Pd G2
• SPhos Pd G2