2-(Dicyclohexylphosphino)biphenyl

1. Ligand used in the palladium-catalyzed synthesis of aromatic amines from aryl chlorides, bromides and triflates.
2. Ligand employed in Suzuki coupling reactions involving aryl chlorides, bromides and triflates.
3. Useful ligand for the Pd-catalyzed oxidation of alcohols in the presence of chlorobenzenes.
4. Useful ligand for the Pd-catalyzed amination with ammonia equivalents.
5. Ligand for the gold(I)-catalyzed intramolecular [4+2] cycloadditions involving 1,3-enynes and arylalkynes with alkenes.
6. Ligand used in the palladium-catalyzed borylation of aryl bromdies.
7. Ligand used in the palladium-catalyzed siliylation of aryl chlorides.

2052-07-5

829-84-5

247940-06-3

General procedure for the synthesis of 2-(dicyclohexylphosphino)biphenyl from 2-bromobiphenyl and dicyclohexylphosphine: under nitrogen protection, a mixture of L1 (0.05 or 0.10 mmol P), [PdCl(η3-C3H5)]2 (0.025 mmol), 2-bromobiphenyl (0.55 mmol) and dicyclohexylphosphine (0.50 mmol) was reacted in a 20 M KOH The mixture in aqueous solution (0.5-1.0 mL) was reacted by shaking at 100 °C for several hours. After completion of the reaction, the mixture was cooled to room temperature and filtered. The aqueous filtrate was extracted with degassed toluene (2 mL x 2 times). For the recovered catalyst resin beads, extract with degassed toluene (2 mL x 4 times). All extracts were combined and dried with anhydrous Na2SO4, followed by concentration under vacuum to obtain the crude product. The crude product was purified by silica gel fast chromatography using degassed eluent (n-hexane/Et2O = 10/0-9/1), and the purification process was completed by a YAMAZEN medium-pressure liquid chromatography system, which ultimately yielded the target product 2-(dicyclohexylphosphino)biphenyl.