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Merck
CN

768154

AdBrettPhos

95%, solid

Synonym(s):

Di-Ad-BrettPhos

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About This Item

Empirical Formula (Hill Notation):
C43H61O2P
CAS Number:
Molecular Weight:
640.92
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22
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Product Name

AdBrettPhos, 95%

Quality Level

product line

Buchwald Ligand

assay

95%

form

solid

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: ligand

mp

231-235 °C

functional group

phosphine

SMILES string

COc1ccc(OC)c(c1P(C23CC4CC(CC(C4)C2)C3)C56CC7CC(CC(C7)C5)C6)-c8c(cc(cc8C(C)C)C(C)C)C(C)C

InChI

1S/C43H61O2P/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/h9-10,17-18,25-33H,11-16,19-24H2,1-8H3

InChI key

NMGHOZQCYNKWBG-UHFFFAOYSA-N

General description

AdBrettPhos is a phosphine-based ligand used in the direct monoarylation of ammonia and suppresses diarylation. In addition, it is a good ligand for five-membered heteroarene couplings and is employed in the preparation of phosphine-ligated palladium complexes to facilitate C-N coupling reactions.

Application

AdBrettPhos can be used as an effective ligand for synthesizing [(L·Pd)n ·(1,5-cyclooctadiene)] pre-catalyst that can be used for the Pd-catalyzed fluorination of aryl triflates.

AdBrettPhos has been used in the Palladium-Catalyzed C-O Cross-Coupling of Primary Alcohols.


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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Articles

Discover AdQPhos and its Pd pre-catalysts for selective α-arylation of diverse nucleophiles under mild aqueous conditions without hazardous solvents.

Related Content

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

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.


A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation
Angewandte Chemie (International Edition in English), 51, 1-5 (2012)
Structure and reactivity of [(L?Pd)n?(1,5-cyclooctadiene)] (n = 1?2) complexes bearing biaryl phosphine ligands
Lee HG, et al.
Inorganica chimica acta, 422, 188-192 (2014)



Global Trade Item Number

SKUGTIN
768154-500MG04061833441107
768154-100MG04061833441091
768154-1G04061826654651