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Key Documents

936189

Sigma-Aldrich

AdQPhos

Synonym(s):

1,2,3,4,5-Pentaphenyl-1′-(di-adamantylphosphino)ferrocene

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About This Item

Empirical Formula (Hill Notation):
C60H59FeP
Molecular Weight:
866.93
UNSPSC Code:
12352142
NACRES:
NA.22

Assay

≥90%

Quality Level

reaction suitability

reaction type: Cross Couplings

functional group

phosphine

SMILES string

c1(C2=CC=CC=C2)c(C3=CC=CC=C3)c(C4=CC=CC=C4)c(C5=CC=CC=C5)c1C6=CC=CC=C6.c7(P([C@]89C[C@H]%10C[C@H](C[C@H](C%10)C9)C8)[C@]%11%12C[C@H]%13C[C@H](C[C@H](C%13)C%12)C%11)cccc7.[Fe]

General description

The precatalysts derived from AdQPhos exhibit excellent activity towards palladium-catalyzed α-arylation reactions under milder conditions. The strength of these catalytic systems in enabling such reactions were demonstrated with the broad scope of nucleophiles, including nitroalkanes, nitriles, amides, esters, and ketones. Compared to other state-of-the-art catalysts, this system was far superior and served as the first versatile catalytic system to accommodate all these nucleophiles in this context.

Further, by merging with micellar catalysis, this catalytic system demonstrated the feasibility of enabling α-arylation reactions under mild aqueous conditions. This approach provides an environmentally benign alternative to toxic/hazardous solvents like 1,4-dioxane or NMP, bringing modern organic synthesis closer to being ideally sustainable.

Application

In addition to facilitating α-arylations, these catalysts demonstrate compatibility with various challenging cross-coupling reactions, such as Suzuki-Miyaura, Buchwald-Hartwig aminations, and C-O and C-S cross-couplings.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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