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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 Code

13 - Non 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
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
Noah P Tu et al.
Angewandte Chemie (International ed. in English), 58(24), 7987-7991 (2019-03-21)
Technologies that enable rapid screening of diverse reaction conditions are of critical importance to methodology development and reaction optimization, especially when molecules of high complexity and scarcity are involved. The lack of a general solid dispensing method for chemical reagents
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