Di(1-adamantyl)benzylphosphine
[CAS# 395116-70-8]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Di(1-adamantyl)benzylphosphine
• Synonyms: bis(1-adamantyl)-benzylphosphane
• Molecular Formula: C₂₇H₃₇P
• Molecular Weight: 392.56
• CAS Registry Number: 395116-70-8
• SMILES: C1C2CC3CC1CC(C2)(C3)P(CC4=CC=CC=C4)C56CC7CC(C5)CC(C7)C6

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

Di(1-adamantyl)benzylphosphine is a noteworthy chemical compound in the field of organophosphorus chemistry, renowned for its distinctive structure and significant applications in catalysis and materials science. The compound features a phosphine group attached to a benzyl group, with two adamantyl groups providing notable steric effects. This unique structure imparts special properties that make it valuable in various chemical processes.

The discovery of di(1-adamantyl)benzylphosphine is part of ongoing research into phosphine ligands, which are essential in coordination chemistry and catalysis. The adamantyl groups were introduced to enhance the steric bulk around the phosphorus center, which can influence the ligand's electronic properties and its interaction with metal centers. This design aims to improve the ligand's performance in catalytic reactions by providing better stabilization of metal complexes.

The synthesis of di(1-adamantyl)benzylphosphine involves several steps. Initially, the synthesis begins with the preparation of the benzylphosphine precursor. This is typically achieved by reacting benzyl chloride with a phosphine source in the presence of a suitable base. The resulting benzylphosphine is then reacted with adamantyl bromide or chloride in the presence of a palladium catalyst to introduce the adamantyl groups. The reaction conditions, such as temperature and solvent, are optimized to achieve high yield and purity of the final product. Characterization of di(1-adamantyl)benzylphosphine is carried out using techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry to confirm its structure.

Di(1-adamantyl)benzylphosphine is widely used as a ligand in various catalytic processes. Its bulky adamantyl groups provide significant steric hindrance, which can influence the electronic environment of the phosphorus atom and the metal center it coordinates with. This steric effect is particularly useful in facilitating certain chemical reactions by stabilizing intermediates and transition states. One notable application of this ligand is in palladium-catalyzed cross-coupling reactions, such as the Suzuki and Heck reactions. In these reactions, di(1-adamantyl)benzylphosphine helps in forming carbon-carbon bonds, which are crucial in the synthesis of complex organic molecules.

In addition to its role in cross-coupling reactions, di(1-adamantyl)benzylphosphine is employed in other catalytic processes, including hydrogenation and hydroformylation. The compound’s ability to form stable complexes with transition metals and its influence on the reactivity of these metals make it a valuable tool in developing new chemical transformations. The ligand’s steric properties also contribute to selectivity in catalytic reactions, allowing for the precise control of product formation.

The compound’s applications extend beyond catalysis to materials science. Di(1-adamantyl)benzylphosphine is used in the design and synthesis of phosphine-based polymers and materials. The ligand’s steric and electronic properties can be leveraged to develop materials with specific characteristics, such as enhanced thermal stability or unique optical properties. These materials have potential applications in sensors, electronic devices, and advanced coatings.

Despite its advantages, the use of di(1-adamantyl)benzylphosphine involves challenges related to its synthesis and handling. The steric bulk of the adamantyl groups can complicate the synthesis process, requiring careful optimization of reaction conditions. Additionally, the compound’s performance in catalytic reactions may need to be fine-tuned to achieve optimal results.

Future research on di(1-adamantyl)benzylphosphine may focus on exploring new applications and optimizing its performance in various chemical processes. The development of new derivatives with modified functional groups could further enhance the compound’s utility in catalysis and materials science. Ongoing studies may also address challenges related to the synthesis and application of this ligand, leading to new innovations and advancements in the field of organophosphorus chemistry.

References

2023. Discovery and synthesis of atropisomerically chiral acyl-substituted stable vinyl sulfoxonium ylides. Nature Chemistry, 15(12).
DOI: 10.1038/s41557-023-01358-z

2004. Homogeneous Catalysts Supported on Soluble Polymers: Biphasic Suzuki-Miyaura Coupling of Aryl Chlorides Using Phase-Tagged Palladium-Phosphine Catalysts. Chemistry (Weinheim an der Bergstrasse, Germany), 10(6).
DOI: 10.1002/chem.200305562