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768154

Sigma-Aldrich

AdBrettPhos

95%

Synonym(s):

Di-Ad-BrettPhos

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About This Item

Empirical Formula (Hill Notation):
C43H61O2P
CAS Number:
1160861-59-5
Molecular Weight:
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

Product No.
Description
Pricing

918008

GPhos, ≥95%

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
SHBQ7846
SHBQ6243
SHBN4009
SHBN1318
SHBL9653

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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)
A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation
Angewandte Chemie (International Edition in English), 51, 1-5 (2012)
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
Biaryl monophosphine ligands in palladium-catalyzed C-N coupling: An updated User's guide
Ingoglia BT, et al.
Tetrahedron, 75(32), 4199-4211 (2019)
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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