tBuBrettPhos Pd G3

• CAS: 1536473-72-9
• Catalog Number: ACM1536473729
• Category: Main Products
• Molecular Weight: 855.4
• Molecular Formula: C44H63NO5PPdS
• Synonyms: Ditert-butyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;methanesulfonic acid;palladium;2-phenylaniline
• Canonical SMILES: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C(C)(C)C)C(C)(C)C)OC)OC)C(C)C.CS(=O)(=O)O.C1=CC=C([C-]=C1)C2=CC=CC=C2N.[Pd]
• InChI: InChI=1S/C31H49O2P.C12H10N.CH4O3S.Pd/c1-19(2)22-17-23(20(3)4)27(24(18-22)21(5)6)28-25(32-13)15-16-26(33-14)29(28)34(30(7,8)9)31(10,11)12;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h15-21H,1-14H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;-1
• InChI Key: VKLHIPFGYVFUGT-UHFFFAOYSA-N
• Melting Point: 119-131 °C
• Appearance: Solid
• Application: Palladium catalyst used for the arylation of primary amides.; ; Palladium catalyst used for the synthesis of N-aryl carbamates.; ; Palladium catalyst used for the N-monoarylation of amidines.; ; Palladium catalyst used for the cross-coupling of aryl chlorides and triflates with sodium cyanate - a practical synthesis of unsymmetrical ureas.; ; Palladium catalyst used in the synthesis of imidazo[4,5-b]pyridines and imidazo[4,5]pyrazines through amidation of 2-chloro-3-amino-heterocycles.; ; Palladium catalyst used in the N-arylation of 2-aminothiazoles; ; Palladium catalyst used in the synthesis of diarylethers under mild conditions.; ; Palladium catalyst used in the hydroxylation of aryl and heteroaryl halides.
• Exact Mass: 854.31994
• Hydrogen Bond Acceptor Count: 7
• Hydrogen Bond Donor Count: 2
• Monoisotopic Mass: 854.31994
• Rotatable Bond Count: 10
• Topological Polar Surface Area: 107 Ų

Case Study

tBuBrettPhos Pd G3-Catalyzed Preparation of Phenols Using Benzaldehyde Oxime as A Hydroxide Surrogate

Fier, Patrick S.,et al. Angewandte Chemie, 2017, 129(16), 4549-4553.

This work reported a designed and broadly applicable Pd-catalyzed method for the preparation of phenols using benzaldehyde oxime as a hydroxide surrogate. This method addresses the shortcomings of previous hydroxylation reactions by avoiding strong basic conditions and avoiding Ar-Pd-OH species as catalytic intermediates.
Based on the results of high-throughput experiments, the most promising lead compounds were investigated: two bases (Cs2CO3, K3PO4), two solvents (DMF, 2-MeTHF), and 24 Pd G3 precatalysts (including tBuBrettPhos Pd G3).
The generality of the reaction was explored, including the intrinsic properties of aryl halides, tolerance to common functional groups, and the ability to couple aryl bromides and aryl chlorides. The results show that the reaction generates phenol products in high yields in the presence of esters, ketones, aldehydes, nitriles, and common heterocycles. Using RockPhos as the ligand, ortho-alkyl-substituted aryl halides were coupled in moderate yields (65%), but using the smaller tBuBrettPhos ligand instead, 2-bromotoluene was coupled in 88% yield.

Cross-Coupling Reactions of tBuBrettPhos Pd G3 in Combination with P2Et Phosphazene

Buitrago Santanilla, Alexander, et al. Organic Letters, 2015, 17(13), 3370-3373.

P2Et phosphazene is a non-nucleophilic organic superbase that can be used in combination with tBuXPhos or tBuBrettPhos G3 precatalysts for a variety of palladium-catalyzed cross-coupling reactions, including C-C, C-N, and C-O couplings of aryl chlorides, bromides, and iodides at room temperature.
The relative reactivity of different aryl electrophiles with the P2Et base was assessed by testing 3-pyridyl bromide, chlorine, and iodine with seven representative nucleophiles. All electrophilic coupling partners achieved complete conversion and high yields with each nucleophile in either DMSO or tert-amyl alcohol, utilizing 1 to 5 mol % of catalyst (tBuXPhos, tBuBrettPhos Pd G3). The P2Et system represents the first non-nucleophilic, soluble coupling conditions at ambient temperature for most nucleophile couplings described in this study, which could significantly impact complex synthetic applications, including natural product synthesis and drug discovery.
The P2Et system was also evaluated for its promise to be mild enough to hydroxylate heteroaryl bromide 13 in the presence of alkyl and aryl esters. Indeed, the desired hydroxypyridine 18 was formed cleanly without contact with the ester.

Custom Q&A

What is the molecular formula of tBuBrettPhos Pd G3?

The molecular formula of tBuBrettPhos Pd G3 is C44H63NO5PPdS.

When was tBuBrettPhos Pd G3 created?

tBuBrettPhos Pd G3 was created on March 1, 2015.

What is the molecular weight of tBuBrettPhos Pd G3?

The molecular weight of tBuBrettPhos Pd G3 is 855.4 g/mol.

What are the component compounds of tBuBrettPhos Pd G3?

The component compounds of tBuBrettPhos Pd G3 include Methanesulfonic Acid, 2-Aminobiphenyl, Palladium, and Di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine.

What is the IUPAC name of tBuBrettPhos Pd G3?

The IUPAC name of tBuBrettPhos Pd G3 is ditert-butyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;methanesulfonic acid;palladium;2-phenylaniline.

What is the InChI key of tBuBrettPhos Pd G3?

The InChI key of tBuBrettPhos Pd G3 is VKLHIPFGYVFUGT-UHFFFAOYSA-N.

What is the Canonical SMILES of tBuBrettPhos Pd G3?

The Canonical SMILES of tBuBrettPhos Pd G3 is CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C(C)(C)C)C(C)(C)C)OC)OC)C(C)C.CS(=O)(=O)O.C1=CC=C([C-]=C1)C2=CC=CC=C2N.[Pd].

What is the CAS number of tBuBrettPhos Pd G3?

The CAS number of tBuBrettPhos Pd G3 is 1536473-72-9.

How many hydrogen bond acceptor counts does tBuBrettPhos Pd G3 have?

tBuBrettPhos Pd G3 has 7 hydrogen bond acceptor counts.

What is the topological polar surface area of tBuBrettPhos Pd G3?

The topological polar surface area of tBuBrettPhos Pd G3 is 107 Ų.