246158-59-8

Basic information

• Product Name: 2-(2-DICYCLOHEXYLPHOSPHINOPHENYL)-1 3-D&
• Synonyms: 2-(2-DICYCLOHEXYLPHOSPHINOPHENYL)-1 3-D&;2-(2-Dicyclohexylphosphinophenyl)-1,3-dioxolane 97%;(2-(1,3-Dioxolan-2-yl)phenyl)dicyclohexylphosphine;2-(2-Dicyclohexylphosphinophenyl)-1,3-dioxolane,97%
• CAS NO: 246158-59-8
• Molecular Formula: C₂₁H₃₁O₂P
• Molecular Weight: 346.448
• Product Categories: Achiral Phosphine;Aryl Phosphine
• Mol File: 246158-59-8.mol

Chemical Properties

• Melting Point: 82-85 °C(lit.)
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-(2-DICYCLOHEXYLPHOSPHINOPHENYL)-1 3-D&(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-DICYCLOHEXYLPHOSPHINOPHENYL)-1 3-D&(246158-59-8)
• EPA Substance Registry System: 2-(2-DICYCLOHEXYLPHOSPHINOPHENYL)-1 3-D&(246158-59-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 246158-59-8(Hazardous Substances Data)

Usage

Uses

Ligand for preparation of palladium P,O-ligand-catalyst for Suzuki cross-coupling reactions.

Upstream product

• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 16523-54-9 chlorodicyclohexylphosphane 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 226089-17-4 2-[bis(cyclohexyl)phosphino]benzaldehyde 

Relevant articles and documents

Novel sulfinyl imine ligands for asymmetric catalysis

(Matrix presented) A novel class of P,N-sulfinyl imine ligands has been prepared that incorporates chirality solely at sulfur. The Pd complex of ligand 14 catalyzes the allylic alkylation reaction with high enantioselectivity (94%), and the first crystal structure of a Pd-bound sulfinyl imine provides insight into binding mode and origins of stereoselectivity.

Palladium/P,O-Ligand-Catalyzed Suzuki Cross-Coupling Reactions of Arylboronic Acids and Aryl Chlorides. Isolation and Structural Characterization of (P,O)-Pd(dba) Complex

The phenyl backbone-derived P,O-ligands 1 and 2 were investigated for their utility as ligands in palladium/ligand-catalyzed Suzuki reactions. The 2-(2′-dicyclohexylphosphinophenyl)-2-methyl-1,3-dioxolane (ligand 1) in combination with Pd(dba)2 affords an efficient catalyst for general Suzuki reactions of a wide variety of arylboronic acids and aryl chlorides, bromides, and iodides to afford the desired biaryl products in high isolated yields. Arylboronic acids and aryl chlorides containing electron-poor, electron-rich, and ortho substituents participate effectively. In contrast, the structurally related ligand 2-(2′-dicyclohexylphosphinophenyl)-1,3-dioxolane (ligand 2) was found to be less efficient under similar conditions. The reaction of ligand 1 with Pd(dba)2 affords the complex LPd-(dba) (14, L = 1). The NMR spectroscopic and X-ray crystallographic data of complex 14 establish that ligand 1 functions as a P,O-chelating ligand in complex 14. The reaction of ligand 2 (2 equiv) with Pd(dba)2 and excess 4-tBu-C6H4Br or the ligand displacement reaction of {Pd[P(o-tolyl)3](4-tBu-C6H4)(μ-Br)} 2 with ligand 2 affords the bis-phosphine complex L2Pd(4-tBu-C6H4)(Br) (13, L = 2). The NMR spectroscopic data of complex 13 establish that ligand 2 in complex 13 functions as a nonchelating ligand. Thus, the higher efficiency of ligand 1 over ligand 2 in Pd/L-catalyzed Suzuki arylation of aryl chlorides can be ascribed to the ability of ligand 1 to generate and stabilize monophosphine P,O-chelating Pd/L intermediates, which appear to be most suitable for Suzuki arylation reactions involving certain substrates and conditions.