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768154

Sigma-Aldrich

AdBrettPhos

95%

Sinónimos:

Di-Ad-BrettPhos

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About This Item

Fórmula empírica (notación de Hill):
C43H61O2P
Número de CAS:
1160861-59-5
Peso molecular:
640.92
UNSPSC Code:
12352112
PubChem Substance ID:
329767360
NACRES:
NA.22

Quality Level

100

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.

related product

Referencia del producto
Descripción
Precios

918008

GPhos, ≥95%

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
Biaryl monophosphine ligands in palladium-catalyzed C-N coupling: An updated User's guide
Ingoglia BT, et al.
Tetrahedron, 75(32), 4199-4211 (2019)
Joseph M Dennis et al.
Journal of the American Chemical Society, 140(13), 4721-4725 (2018-03-13)
Due to the low intrinsic acidity of amines, palladium-catalyzed C-N cross-coupling has been plagued continuously by the necessity to employ strong, inorganic, or insoluble bases. To surmount the many practical obstacles associated with these reagents, we utilized a commercially available
Hong Zhang et al.
Organic letters, 20(6), 1580-1583 (2018-02-24)
Two catalyst systems are described, which together provide mild and general conditions for the Pd-catalyzed C-O cross-coupling of primary alcohols. For activated substrates, such as electron-deficient aryl halides, the commercially available ligand L2 promotes efficient coupling for a variety of

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Buchwald and non-Buchwald catalysts and ligands for pharma or industrial chemistry applications

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Buchwald and non-Buchwald catalysts and ligands for pharma or industrial chemistry applications

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.

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