CAS 166330-10-5 (Oxybis(2,1-phenylene))bis(diphenylphosphine)

IUPAC Name

[2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane;

Molecular Weight

538.567g/mol

Molecular Formula

C36H28OP2;

Canonical SMILES

C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6;

InChI

InChI=1S/C36H28OP2/c1-5-17-29(18-6-1)38(30-19-7-2-8-20-30)35-27-15-13-25-33(35)37-34-26-14-16-28-36(34)39(31-21-9-3-10-22-31)32-23-11-4-12-24-32/h1-28H;

InChI Key

RYXZOQOZERSHHQ-UHFFFAOYSA-N;

Complexity

594

Covalently-Bonded Unit Count

Exact Mass

538.162g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

538.162g/mol

Rotatable Bond Count

Topological Polar Surface Area

9.2A^2

Application

(Oxybis(2,1-phenylene))bis(diphenylphosphine) serves as a versatile ligand demonstrated to enhance catalytic efficiency across a broad range of chemical reactions. It appears as a white to off-white crystalline powder and plays a critical role in multiple applications, such as facilitating ruthenium-catalyzed greener amine synthesis from amines and alcohols using hydrogen-borrowing techniques. Additionally, it's involved in the N-alkylation of amines and sulfonamides via borrowing hydrogen methodology and is an effective ligand in Pd-catalyzed formation of diaryl amines. The product finds utility in the C3 benzylation of indoles and monoallylation of ammonia. It is employed in palladium-catalyzed aerobic oxidation coupling of acyl chlorides with arylboronic acids, the carbonylation of aryl iodides, and direct C-H arylation of benzothiodiazoles. Other notable uses include its role in stereo-retentive azacyclization of propargylic carbonates and benzyne trimerization catalyzed by palladium.

February 7, 2025

Excellent Ligand for Advanced Catalysis

I've used (Oxybis(2,1-phenylene))bis(diphenylphosphine) in our lab. It excels as a ligand for diverse reactions, including ruthenium-catalyzed N-alkylation and Pd-catalyzed diaryl amine formation. The enhanced catalytic efficiency was remarkable in our experiments.