1262046-34-3

Usage

Uses

Used in Organic Synthesis:
Rockphos is used as a catalyst in organic reactions for the formation of carbon-carbon and carbon-heteroatom bonds. Its ability to work alongside a palladium compound catalyst makes it a valuable tool in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
Rockphos is used as a catalyst in the 2-fluoroethoxylation of bromo-chalcones in the presence of a palladium catalyst. This application is particularly relevant in the development of new pharmaceutical compounds, as it allows for the creation of novel molecular structures with potential therapeutic properties.
Used in Chemical Research:
In the field of chemical research, Rockphos is employed in the conversion of aryl chlorides into aryl methoxides using RockPhos Pd G3 as a catalyst. This reaction is crucial for the synthesis of various organic compounds, including those with potential applications in materials science, pharmaceuticals, and other industries.
Overall, Rockphos is a versatile and valuable compound in the realm of organic chemistry, with applications spanning across various industries due to its ability to enhance the efficiency and selectivity of palladium-catalyzed reactions.

Reaction

Ligand used in the palladium-catalyzed C-O bond forming reactions of secondary and primary alcohols with a range of aryl halides. Heterocyclic halides and, for the first time, electron-rich aryl halides can be coupled with secondary alcohols.

Upstream product

• 13716-10-4 di(tert-butyl)chlorophosphine 
• 1351403-03-6 2-iodo-2',4',6'-triisopropyl-3-methoxy-6-methyl-1,1'-biphenyl 
• 452-78-8 3-fluoro-4-methyl phenol 
• 21524-34-5 2,4,6-triisopropyl-1-bromobenzene 
• 405-06-1 2-fluoro-4-methoxy-1-methylbenzene 
• 108894-99-1 (2,4,6-triisopropylphenyl)magnesium bromide 
• 108-86-1 bromobenzene 
• 1402393-57-0 2-bromo-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl 

Downstream Products

• 1345093-35-7 PdBrC₆H₄(CH₂)3CH₃C₆H₂(CH(CH₃)2)3C₆H₂OCH₃CH₃P(C(CH₃)3)2 
• 1345093-36-8 PdFC₆H₄(CH₂)3CH₃C₆H₂(CH(CH₃)2)3C₆H₂OCH₃CH₃P(C(CH₃)3)2 

Relevant academic research and scientific papers

Pd-Catalyzed Etherification of Nitroarenes

The Pd-catalyzed etherification of nitroarenes with arenols has been achieved using a new rationally designed ligand. Mechanistic insights were used to design the ligand so that both the oxidative addition and reductive elimination steps of a plausible catalytic cycle were facilitated. The catalytic system established here provides direct access to a range of unsymmetrical diaryl ethers from nitroarenes.

An improved synthesis of brettphos- and rockphos-type biarylphosphine ligands

Improved processes for the preparation of biphenyl-based phosphine ligands t-BuBrettPhos, RockPhos, and BrettPhos are presented. The new methods, featuring the use of Grignard reagents and catalytic amounts of copper, are superior to the previous methods, which require the use of tert-butyllithium and stoichiometric amounts of copper. Specifically, the use of less dangerous reagents provides a safer process, while the use of catalytic amounts of copper allows for the isolation of pure products in high yield. These improvements are particularly significant for the large-scale preparation of these ligands. Copyright

A single phosphine ligand allows palladium-catalyzed intermolecular C-O bond formation with secondary and primary alcohols

Forging a bond: An efficient, general palladium catalyst for C-O bond-forming reactions of secondary and primary alcohols with a range of aryl halides has been developed using the ligand 1. Heteroaryl halides, and for the first time, electron-rich aryl halides can be coupled with secondary alcohols. A diverse set of substrate combinations are possible with just a single ligand, thus obviating the need to survey multiple ligands. Copyright

Evidence for in situ catalyst modification during the Pd-catalyzed conversion of aryl triflates to aryl fluorides

A mechanistic investigation of the Pd-catalyzed conversion of aryl triflates to fluorides is presented. Studies reveal that C-F reductive elimination from a LPdII(aryl)F complex (L = t-BuBrettPhos or RockPhos) does not occur when the aryl group is electron rich. Evidence is presented that a modified phosphine, generated in situ, serves as the actual supporting ligand during catalysis with such substrates. A preliminary study of the reactivity of a LPdII(aryl)F complex based on this modified ligand is reported.