4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

Description

XantPhos is a bidentate bis-phosphine ligand with a wide bite angle. XantPhos is commonly used as a ligand in palladium catalyzed cross-coupling reactions such as Buchwald reactions.

Chemical properties

White to light yellow crystals

The Uses of 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

suzuki reaction

The Uses of 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

4,5-Bis(diphenylphosphino)-9, 9-dimethylxanthene is used as a bidentate ligand, which finds application in hydroformylation of alkenes.

The Uses of 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenyl-phosphine is an organophosphorus compound derived from the heterocycle xanthene. It is used as a bidentate ligand and is noteworthy for having a particularly wide bite angle. Such ligands are useful in the hydroformylation of alkenes.

Reactions

1. Ligand used for the hydroformylation of alkenes.
2. Ligand used in the intermolecular coupling of amides and hydrazones with aryl halides.
3. Ligand used in the intermolecular coupling of amides with aryl halides or triflates.
4. Ligand used in the coupling of heteroarylamines and aryl halides.
5. Ligand used in the hydrophosphinylation of alkenes and alkynes.
6. Ligand used for the Au(I)-catalyzed dehydrogenative silation of alcohols.
7. Ligand used for the sulfinylation of aryl iodides.
8. Ligand used for the Pd-catalyzed carbonylation reaction of aryl bromides and amines.
9. Ligand used for the Ni-cataltzed alkynylcyanation of alkynes.
10. Ligand used for the Pd-catalyzed N-arylation of 3-amino-1H-pyrazole.
11. Ligand used for the Rh-catalyzed dehydrogenation borylation of cyclic alkenes.
12. Ligand used for the Pd-catalyzed intermolecular coupling of H-Phosphonate diesters with benzyl halides.
13. Ligand used for the Pd-catalyzed one pot synthesis of 4-aryl-1H-1,2,3-triazoles.
14. Ligand used for the Pd-catalyzed intermolecular addition of formamides to alkynes.
15. Ligand used for the Pd-catalyzed decarboxylative couplings of 2-(2-azaaryl)acetates with aryl halides and triflates.
16. Ligand used for the Pd-catalyzed benzylic arylation of 2-methyl azaarenes
17. Ligand used for the Pd-catalyzed α-arylation of heteroaromatic ketones.
18. Ligand used for the Pd-catalyzed direct alkynlation of both azoles and azolines.
19. Ligand used for the Cu-catalyzed intermolecular coupling of alkynes with aryl iodides.
20. Ligand used for the Pd-catalyzed ene-type reaction of aldehydes with 1,3-diene.
21. Ligand used for the Ru-catalyzed intermolecular addition of 2-phenylbenzoic acid onto unactivated olefins.
22. Ligand used for the Pd/Cu-catalyzed direct arylation of heteroarenes.
23. Ligand used for the Pd-catalyzed reaction of propargyl-substituted malonate esters with aryl halides.
24. Ligand used for the Pd-catalyzed decarboxylative coupling of tertiary cyanoacetate salts with aryl halides and triflates.
25. Ligand used for the Pd-catalyzed hydroesterification of alkynes.
26. Ligand used for the Cu-catalyzed arylation of arylboronic acids with aldehydes.
27. Ligand used for the Ru-catalyzed oxidative synthesis of heterocycles from alcohols.
28. Ligand used for the Rh-catalyzed borylation of nitriles.
29. Ligand used in the Pd-catalyzed α-arylation of benzylic phosphine oxides.
30. Ligand used in the Pd-Catalyzed Oxidative Coupling of Enamides and Alkynes.
31. Ligand used in the Pd-catalyzed difunctionalization of enol ethers to amino acetals with aminals and alcohols.
32. Ligand used in the Pd-catalyzed alkoxycarbonylation of α-chloroketones.

Preparation

A mixture of the chloride (25 g, 168 mmol), the amine (40 g, 168 mmol), Pd(OAc)2 (1.5 g, 6.72 mmol), (+-) BINAP (4.18 g, 6.72 mmol), and Cs2CO3 (76.7 g, 235.2 mmol) in toluene (800 mL) was stirred at 90 C under N2 for 23 h. The mixture was filtered through a pad of celite and washed with EtOAc. The filtrate was concentrated in vacuo and purified by silica gel flash chromatography (1:5 EtOAc/petroleum ether) to provide the product as a red solid. [22.4 g, 37%]