776106

Sigma-Aldrich

AdBrettPhos Pd G3

Synonym(s):
Di-Ad-BrettPhos-G3-Palladacycle, [2-(Di-1-adamantylphosphino)-2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl][2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate
Empirical Formula (Hill Notation):
C56H74NO5PPdS
CAS Number:
Molecular Weight:
1010.65
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

feature

generation 3

reaction suitability

core: palladium
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

mp

251-253 °C

functional group

phosphine

SMILES string

COC1=CC=C(OC)C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)=C1P([C@]34C[C@H]5C[C@H](C[C@H](C5)C4)C3)[C@@]6(C[C@H](C7)C8)CC7C[C@H]8C6.NC9=CC=CC=C9C%10=CC=CC=C%10[Pd]OS(C)(=O)=O

InChI

1S/C43H61O2P.C12H10N.CH4O3S.Pd/c1-25(2)34-17-35(26(3)4)39(36(18-34)27(5)6)40-37(44-7)9-10-38(45-8)41(40)46(42-19-28-11-29(20-42)13-30(12-28)21-42)43-22-31-14-32(23-43)16-33(15-31)24-43;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h9-10,17-18,25-33H,11-16,19-24H2,1-8H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

OZFYYHNERORONM-UHFFFAOYSA-M

Application

Buchwald 3rd Generation Pd Precatalyst adorned by the bulk di-adamntyl BrettPhos ligand. This complex has been used in the monoarylation of ammonia, displaying apptitude for otherwise difficult 5-member heterocyclic substrates.

Mild and Highly Selective Palladium-Catalyzed Monoarylation of Ammonia Enabled by the Use of Bulky Biarylphosphine Ligands and Palladacycle Precatalysts

Packaging

100, 500 mg in glass bottle
2, 5 g in glass bottle

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Articles
G3 and G4 Buchwald palladium precatalysts are the newest air, moisture, and thermally stable crossing-coupling complexes used in bond formation for their versatility and high reactivity.
Read More
Related Content
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.
Read More

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