[(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride
[CAS# 115826-95-4]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: [(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride
• Synonyms: BINAP-PdCl2
• Molecular Formula: C₄₄H₃₂Cl₂P₂Pd
• Molecular Weight: 800.00
• CAS Registry Number: 115826-95-4
• EC Number: 621-611-4
• SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.Cl[Pd]Cl

Properties

• Melting point: 230-300 °C (decomp.) (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

[(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride, commonly referred to as a palladium catalyst with a chiral ligand, is an important compound in the field of organometallic chemistry. It is known for its ability to catalyze a variety of reactions, especially those that require the formation of carbon-carbon bonds, such as asymmetric hydrogenation and cross-coupling reactions.

The discovery and development of chiral palladium catalysts like [(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride can be traced back to the work of researchers in the 1970s and 1980s, who were focused on improving the selectivity and efficiency of palladium-based catalysts. One of the key breakthroughs during this period was the introduction of chiral ligands, such as binaphthyl-based phosphines, which could impart chirality to the catalyst and enable asymmetric synthesis.

[(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride is a representative example of such a chiral palladium complex, where the (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl ligand coordinates with a palladium center to create a highly efficient catalyst. The chiral nature of the ligand is crucial, as it allows the catalyst to discriminate between different enantiomers of substrates, making it highly valuable in the synthesis of optically active compounds.

This compound is primarily used in asymmetric catalysis, particularly in reactions such as the asymmetric hydrogenation of alkenes and imines, as well as in Suzuki-Miyaura cross-coupling reactions. The ability to catalyze the formation of chiral centers with high enantioselectivity has made [(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride a powerful tool in both synthetic organic chemistry and the pharmaceutical industry, where the preparation of enantiomerically pure compounds is often essential.

In the Suzuki-Miyaura reaction, which is widely used for forming carbon-carbon bonds, this palladium complex can catalyze the coupling of aryl or vinyl boronic acids with halides. The application of this reaction in the synthesis of biaryls, pharmaceuticals, and other organic materials is significant. The high selectivity and efficiency of [(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride have made it an indispensable catalyst in modern organic synthesis.

The complex is also of interest in the development of new materials and fine chemicals. Its ability to mediate reactions under mild conditions and with high stereoselectivity is crucial for producing specialty chemicals, including those used in the production of high-performance polymers and other advanced materials. Additionally, its role in asymmetric synthesis contributes to the production of chiral intermediates that are necessary for the synthesis of a wide range of bioactive compounds.

Overall, [(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride is a highly valuable catalyst in the field of organometallic chemistry, offering significant advantages in asymmetric synthesis and cross-coupling reactions. Its discovery and development have been instrumental in advancing synthetic methods for the creation of complex, chiral molecules, with important applications in both industrial and pharmaceutical contexts.

References

2004. A highly efficient asymmetric Suzuki-Miyaura coupling reaction catalyzed by cationic chiral palladium(ii) complexes. Chemical Communications, (17).
DOI: 10.1039/B407250B

2015. Double [3 + 2]-dimerisation cascade synthesis of bis(triazolyl)bisphosphanes, a new scaffold for bidentate bisphosphanes. Dalton Transactions, 44(28).
DOI: 10.1039/C5DT02197A

2022. Aggregation-induced polarization (AIP) of derivatives of BINOL and BINAP. RSC Advances, 12(46).
DOI: 10.1039/D2RA05597J