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936839

Sigma-Aldrich

AdBrettPhos ChemBeads

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Synonym(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

Empirical Formula (Hill Notation):
C43H61O2P
CAS Number:
1160861-59-5
Molecular Weight:
640.92
UNSPSC Code:
12352100

form

solid

Quality Level

100

composition

, 4-6% (loading)

reaction suitability

reagent type: ligand

SMILES string

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?

InChI key

NMGHOZQCYNKWBG-DQMWLEPPSA-N

General description

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)

related product

Product No.
Description
Pricing

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW6209

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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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