Chemical Properties
white to light yellow crystal powde
Definition
ChEBI: 1,2-bis(diphenylphosphino)ethane is a tertiary phosphine and a member of diphosphanes. It has a role as an allergen.
reaction suitability
reagent type: ligand
reaction type: C-C Bond Formation
reagent type: ligand
reaction type: Carbonylations
reagent type: ligand
reaction type: Cycloadditions
reagent type: ligand
reaction type: Decarboxylations
reagent type: ligand
reaction type: Diels-Alder Reaction
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
Mechanism of action
1,2-Bis(diphenylphosphino)ethane (DPPE) and its synthetic analogues are important structural motifs in organic synthesis, particularly as diphosphine ligands with a C2-alkyl-linker chain. Since DPPE is known to bind to many metal centers in a bidentate fashion to stabilize the corresponding metal complex via the chelation effect originating from its entropic advantage over monodentate ligands, it is often used in transition-metal-catalyzed transformations.
Synthesis
Several synthetic methods to produce 1,2-Bis(diphenylphosphino)ethane (DPPE) exist; however, most of these methods are limited to substitution reactions of highly reactive alkali metal diphenylphosphides (e.g., Ph2PM; M = Li or Cs) with 1,2-dihaloethanes (X−CH2−CH2−X; X = Cl, Br, and I) in an SN2 fashion (Eq. 1). Moreover, there are a few methods using the alkoxide-base (KOt-Bu)-catalyzed hydrophosphination of vinyl phosphines (Eq. 2) with diphenylphosphines9 or the dihydrophosphination of acetylene gas (Eq. 3). [1]
Purification Methods
Recrystallise it from aqueous EtOH or *C6H6. The dimethiodide, when recrystallised from MeOH has m 305-307o, and the dioxide when recrystallised from toluene or DMF (needles), or *C6H6 (plates) has m 252-254o (276-278o) [Isslieb et al. Chem Ber 92 3175 1959, NMR: Aquiar et al. J Org Chem 29 1660 1964, B.ckvall et al. J Org Chem 52 5430 1987]. [Beilstein 16 IV 958.]
References
[1] Takano, H., Katsuyama, H., Hayashi, H. et al. A theory-driven
synthesis of symmetric and unsymmetric 1,2-bis(diphenylphosphino)ethane
analogues via radical difunctionalization of ethylene. Nat Commun 13, 7034 (2022).
