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761605

Sigma-Aldrich

BrettPhos Pd G3

98%

Synonym(s):

[(2-Di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′ -biphenyl)]palladium(II) methanesulfonate methanesulfonate

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About This Item

Empirical Formula (Hill Notation):
C48H66NO5PPdS
CAS Number:
1470372-59-8
Molecular Weight:
906.50
MDL number:
MFCD22572666
UNSPSC Code:
12352300
PubChem Substance ID:
329766562
NACRES:
NA.22

Assay

98%

form

solid

feature

generation 3

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: catalyst
core: palladium
reaction type: Cross Couplings

mp

150-193 °C (decomposition)

functional group

amine

SMILES string

CS(=O)(O[Pd]c1c(c2c(N)cccc2)cccc1)=O.COc3c(P(C4CCCCC4)C5CCCCC5)c(c6c(C(C)C)cc(C(C)C)cc6C(C)C)c(OC)cc3

InChI

1S/C35H53O2P.C12H10N.CH4O3S.Pd/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h19-25,27-28H,9-18H2,1-8H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

PQYBJDCHLVJYSD-UHFFFAOYSA-M

Related Categories

General description

BrettPhos Pd G3 is a third generation (G3) Buchwald precatalyst. It is air, moisture and thermally-stable and is highly soluble in a wide range of common organic solvents. It has long life in solutions. BrettPhos Pd G3 is an excellent reagent for Buchwald-Hartwig cross-coupling reaction. Some of its unique features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Application

BrettPhos Pd G3 may be used for the C-N coupling reaction between monosubstituted ureas and 1,2 dihaloaromatic system to form benzimidazolones.
It may be used in the synthesis of following compounds:
  • [Pd(cinnamyl)(BrettPhos)]OTf by reacting with [(cinnamyl)PdCl]2 and AgOTf.
  • [Pd(crotyl)(BrettPhos)]OTf by reacting with [(crotyl)PdCl]2 and AgOTf.
  • [Pd(allyl)(BrettPhos)]OTf by reacting with [(allyl)PdCl]2 and AgOTf.
  • Pd(allyl)(BrettPhos)Clby reacting with [(allyl)PdCl]2.
For small scale and high throughput uses, product is also available as ChemBeads (928321)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM7894
SHBL4566
SHBJ8190
SHBJ2254
SHBH6803

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Generating Active ?L-Pd (0)? via Neutral or Cationic Π-Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure-Activity Studies in Challenging Cross-Coupling Reactions.
DeAngelis AJ, et al.
The Journal of Organic Chemistry, 80(13), 6794-6813 (2015)
Regioselective Synthesis of Benzimidazolones via Cascade C-N Coupling of Monosubstituted Ureas.
Ernst JB, et al.
Organic Letters, 16(14), 3844-3846 (2014)
2-Aminobiphenyl Palladacycles: The ?Most Powerful? Precatalysts in C-C and C-Heteroatom Cross-Couplings.
Bruneau A, et al.
ACS Catalysis, 5(2), 1386-1396 (2015)

Articles

Scale-Up Guide: Buchwald-Hartwig Amination Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

KitAlysis™ C-N (Buchwald-Hartwig) High-Throughput Screening Kit

All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

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Buchwald Group – Professor Product Portal

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

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