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936839

Sigma-Aldrich

AdBrettPhos ChemBeads

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Synonyme(s) :

Di-Ad-BrettPhos ChemBeads, Diadamantan-1-yl)(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane ChemBeads

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About This Item

Formule empirique (notation de Hill):
C43H61O2P
Numéro CAS:
1160861-59-5
Poids moléculaire :
640.92
Code UNSPSC :
12352100

Forme

solid

Niveau de qualité

100

Composition

, 4-6% (loading)

Pertinence de la réaction

reagent type: ligand

Chaîne SMILES 

COC1=CC=C(C(C2=C(C=C(C=C2C(C)C)C(C)C)C(C)C)=C1P([C@]34C[C@H]5C[C@H](C[C@H](C5)C4)C3)[C@]67C[C@H]8C[C@H](C[C@H](C8)C7)C6)OC

InChI

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/t28-,29+,30-,31-,32+,33-,42?,43?,46?

Clé InChI

NMGHOZQCYNKWBG-DQMWLEPPSA-N

Description générale

The AdBrettPhos ligand coated of glass beads. 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. For use in high-throughput expermentation (HTE).

Application

AdBrettPhos has been used in:
C-N Coupling reactions. (see 31896889)
The fluorination of alrl triflates.(see 25346547)
The Palladium-Catalyzed C-O Cross-Coupling of Primary Alcohols. (see 29474078)
ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.
For general uses, product is also available in powdered form (768154)

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

768154

AdBrettPhos, 95%

924377

Palladium(II) Acetate ChemBeads

928364

XPhos ChemBeads

931055

tBuXPhos Pd G3 ChemBeads

Code de la classe de stockage

13 - Non Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
MKCW6209

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Hong Geun Lee et al.
Inorganica chimica acta, 422, 188-192 (2014-10-28)
The structure of the stable Pd(0) precatalyst [(1,5-cyclooctadiene)(L•Pd)2] (L = AdBrettPhos) for the Pd-catalyzed fluorination of aryl triflates has been further studied by solid state NMR and X-ray cystrallography of the analogous N-phenylmaleimide complex. The reactivity of this complex with
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
Bryan T Ingoglia et al.
Tetrahedron, 75(32), 4199-4211 (2020-01-04)
Over the past three decades, Pd-catalyzed cross-coupling reactions have become a mainstay of organic synthesis. In particular, catalysts derived from biaryl monophosphines have shown wide utility in forming C-N bonds under mild reaction conditions. This work summarizes a variety of
Ana L Aguirre et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 27(51), 12981-12986 (2021-07-08)
High-throughput experimentation (HTE) methods are central to modern medicinal chemistry. While many HTE approaches to C-N and Csp2 -Csp2 bonds are available, options for Csp2 -Csp3 bonds are limited. We report here how the adaptation of nickel-catalyzed cross-electrophile coupling of
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