Butyldi-1-adamantylphosphine

Reaction

1. Ligand for the Pd-catalyzed Suzuki coupling reaction.
2. Ligand for the Pd-catalyzed formation of α-aryl ketones.
3. Ligand for the Pd-catalyzed aminations
4. Ligand for the Pd-catalyzed Heck reaction.
5. Ligand used for arylation of benzoic acids.
6. Ligand for the formylation of aryl bromides.
7. Ni-catalyzed denitrogenative alkyne insertion reactions of triazoles.
8. Ligand for palladium-catalyzed aminocarbonylation of aryl halides
9. Palladium-catalyzed direct arylation of oxazole at C-5 with aryl bromides, chlorides, and triflates
10. Palladium-catalyzed carbonylative sonogashira coupling of aryl bromides.

Physical properties

Butyldi-1-adamantylphosphine is a white to yellow solid with a melting point of 100°C and an estimated boiling point of 449.6±12.0°C. Store at room temperature, it is air sensitive.

Uses

CataCXium A is a catalyst. CataCXium A is an electron-rich phosphine ligand used for palladium catalyzed cross-coupling reactions like Heck and Suzuki coupling reactions.

Uses

suzuki reaction

Uses

cataCXium A or di-adamantylalkylphosphine is a bulky and electron-rich phosphine ligand that is highly effective for palladium catalyzed cross-coupling reactions such as Heck and Suzuki coupling, Buchwald-Hartwig amination of aryl chlorides, and α-arylation reactions of ketones.

Other applications:

• palladium-catalyzed carbonylation of aryl and heteroaryl halides
• palladium-catalyzed synthesis of (hetero)aromatic nitriles
• palladium-catalyzed aminocarbonylation of aryl halides

General Description

Sold in collaboration with Solvias AG

reaction suitability

reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-C Bond Formation
reagent type: ligand
reaction type: Cross Couplings
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Synthesis

Phosphonium salt (2.2 mmol) was added to a cooled solution (- 78 C) of Et3N (4.44 g, 44 mmol) in di-n-butyl ether (20 mL). The reaction mixture was stirred at -78 C for 5 h and then allowed to warm gradually to r.t. The solvent was removed under vacuum and the residue was dissolved in degassed EtOH (5 mL). After stirring for 15 min, the solid was filtered off and dried to yield the desired phosphine, which can be further purified by crystallization from EtOH. Butyldi-1-adamantylphosphine, yield 90%.
31P NMR (C6D6)|: 24.9. Mp 108-110C. IR (KBr): 3425 (m, br), 2952 (s), 2847 (s), 2847 (s), 2675 (w), 1446 cm-1 (m). 1H NMR (250 MHz, C6D6): | = 0.96 (3 H, t, 3JH, H = 7.3 Hz, CH3), 1.35-2.03 (36 H, m, adamantyl-30H, butyl-6H). 13C NMR (62 MHz, C6D6): | = 41.3 (d, 2JC,P = 11.3 Hz, C-2), 37.4 (C-4), 36.1 (d, 1JC,P = 23.5 Hz, C-1), 33.9 (d, 1JC,P = 26.2 Hz, butyl-|á -CH2), 29.1 (d, 3JC,P = 7.6 Hz, C-3), 24.9 (d, 2JC,P = 13.1 Hz, butyl-| -CH2), 17.1 (d, 3JC,P = 21.6 Hz, butyl-| -CH2), 14.3 (butyl-CH3). MS (EI, 70 eV): m/z (%) = 358 (M+, 60), 135 (Ad+, 100).

References

[1] Patent: US2004/68131, 2004, A1