936189

AdQPhos

• Synonym(s): 1,2,3,4,5-Pentaphenyl-1′-(di-adamantylphosphino)ferrocene
• Empirical Formula (Hill Notation): C₆₀H₅₉FeP
• Molecular Weight: 866.93
• UNSPSC Code: 12352142

Properties

• assay: ≥90%
• Quality Level: 100
• 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]

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable