(Tbubrettphos PD(allyl))otf
[CAS# 1798782-17-8]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: (Tbubrettphos PD(allyl))otf
• Synonyms: Palladium(1+), [(1,2,3-?)-2-buten-1-yl][[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl-?C1']bis(1,1-dimethylethyl)phosphine-?P]-, 1,1,1-trifluoromethanesulfonate (1:1)
• Molecular Formula: C₃₆H₅₆F₃O₅PPdS
• Molecular Weight: 795.28
• CAS Registry Number: 1798782-17-8
• SMILES: C/C=C/[CH2-].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C(C)(C)C)C(C)(C)C)OC)OC)C(C)C.C(F)(F)(F)S(=O)(=O)[O-].[Pd+2]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Discovory and Applicatios

Tbubrettphos PD(allyl)otf, formally known as [2,2-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(0) tris(2,4,6-tri-t-butylphenyl)phosphate, represents a significant advancement in the field of organometallic chemistry, specifically in the area of catalysis. This compound, with its complex structure and distinct properties, has opened new avenues for research and application, particularly in the synthesis of complex organic molecules.

The discovery of Tbubrettphos PD(allyl)otf can be traced back to the growing need for more efficient and selective catalysts in organic synthesis. Traditional palladium-based catalysts were widely used in various cross-coupling reactions; however, researchers sought compounds that could offer enhanced stability, activity, and selectivity. The introduction of Tbubrettphos PD(allyl)otf emerged from this quest, combining the robustness of palladium with the unique properties of its phosphine ligand.

The synthesis of Tbubrettphos PD(allyl)otf involves the coordination of a palladium center with a bidentate phosphine ligand and an allyl group. The ligand, 2,2-bis(diphenylphosphino)-1,1'-binaphthyl (often abbreviated as Brettphos), is known for its ability to stabilize palladium in its zero oxidation state and impart exceptional catalytic activity. The addition of tris(2,4,6-tri-t-butylphenyl)phosphate as the counterion further enhances the compound's stability and solubility in organic solvents.

One of the most notable applications of Tbubrettphos PD(allyl)otf is in cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are pivotal in the construction of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials. The presence of the bulky t-butyl groups in the phosphate counterion helps in minimizing unwanted side reactions, thereby increasing the selectivity and yield of the desired products.

In addition to cross-coupling reactions, Tbubrettphos PD(allyl)otf has found utility in other areas of organic synthesis. Its ability to facilitate C–C bond formation makes it a valuable tool in the synthesis of complex natural products and polymers. The compound's stability and reactivity profile allow for its use in various conditions, including those involving sensitive functional groups.

Researchers have also explored the potential of Tbubrettphos PD(allyl)otf in catalyzing asymmetric transformations, which are crucial for producing enantiomerically pure compounds. The chirality imparted by the binaphthyl ligand plays a significant role in directing the stereochemical outcome of reactions, making it a valuable asset in the synthesis of chiral drugs and fine chemicals.

Overall, Tbubrettphos PD(allyl)otf represents a significant advancement in catalytic chemistry. Its discovery has provided chemists with a powerful tool for conducting selective and efficient organic transformations. As research continues to explore and expand its applications, Tbubrettphos PD(allyl)otf is poised to make a lasting impact on the field of synthetic chemistry.