677736-23-1

Usage

Uses

Used in Catalyst Synthesis:
CHLORODICARBONYL(1,2,3,4,5-PENTAPHENYLC& is used as a reactant for the synthesis of cyclopentadienyl ruthenium dicarbonyl catalysts. These catalysts are essential in various chemical reactions, particularly in the field of homogeneous catalysis.
Used in Ligand Exchange:
CHLORODICARBONYL(1,2,3,4,5-PENTAPHENYLC& is also utilized in ligand exchange processes, where it can replace other ligands in metal complexes. This property allows for the modification of the electronic and steric properties of the metal center, which can be crucial for optimizing catalytic activity and selectivity.
Used in the Formation of Cyclopentadienyl Ruthenium Alkoxycarbonyl Complexes:
CHLORODICARBONYL(1,2,3,4,5-PENTAPHENYLC& is employed in the formation of cyclopentadienyl ruthenium alkoxycarbonyl complexes with coordinated C:C bonds. These complexes are valuable intermediates in organic synthesis and can be used to construct more complex molecular structures.
Used as a Catalyst in (S)-Selective Dynamic Kinetic Resolution:
CHLORODICARBONYL(1,2,3,4,5-PENTAPHENYLC& serves as a catalyst for the (S)-selective dynamic kinetic resolution of secondary alcohols. This process is an important method for the enantioselective synthesis of chiral compounds, which are widely used in the pharmaceutical and agrochemical industries.
Used in Stereoselective Synthesis of Neonicorinoide Pesticide Derivatives:
CHLORODICARBONYL(1,2,3,4,5-PENTAPHENYLC& is used as a catalyst in the stereoselective synthesis of neonicorinoide pesticide derivatives. This application highlights its potential in the development of new and more efficient methods for the production of agrochemicals.
Used in Divergent Asymmetric Synthesis of 3,5-Disubstituted Piperidines:
CHLORODICARBONYL(1,2,3,4,5-PENTAPHENYLC& is also utilized in the divergent asymmetric synthesis of 3,5-disubstituted piperidines. This application demonstrates its versatility in organic synthesis and its potential to contribute to the development of new pharmaceutical agents and other bioactive molecules.

Upstream product

• 15243-33-1 dodecacarbonyl-triangulo-triruthenium 
• 67-66-3 chloroform 
• 2519-10-0 1,2,3,4,5-pentaphenylcyclopentadiene 

Downstream Products

• 1306623-14-2 chlorocarbonyl([13-C]carbonyl)(η5-pentaphenylcyclopentadienyl)ruthenium(II) 
• 1111635-29-0 (η5-pentaphenylcyclopentadienylato)Ru(CO)2(OC(C6H5)CHCH2) 
• 2387-23-7 1,3-Dicyclohexylurea 
• 1396804-54-8 (η⁵-C₅Ph₅)Ru(CO)₂Cl 
• 860009-17-2 η5-CpPh5Ru(CO)2(t-pentoxide) 
• 860009-16-1 dicarbonyl(η5-pentaphenylcycopentadienyl)(tert-butyloxy)ruthenium(II) 

Relevant academic research and scientific papers

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.

In Situ Structural Determination of a Homogeneous Ruthenium Racemization Catalyst and Its Activated Intermediates Using X-Ray Absorption Spectroscopy

The activation process of a known Ru-catalyst, dicarbonyl(pentaphenylcyclopentadienyl)ruthenium chloride, has been studied in detail using time resolved in situ X-ray absorption spectroscopy. The data provide bond lengths of the species involved in the process as well as information about bond formation and bond breaking. On addition of potassium tert-butoxide, the catalyst is activated and an alkoxide complex is formed. The catalyst activation proceeds via a key acyl intermediate, which gives rise to a complete structural change in the coordination environment around the Ru atom. The rate of activation for the different catalysts was found to be highly dependent on the electronic properties of the cyclopentadienyl ligand. During catalytic racemization of 1-phenylethanol a fast-dynamic equilibrium was observed.

A ruthenium racemisation catalyst for the synthesis of primary amines from secondary amines

A Ru-based half sandwich complex used in amine and alcohol racemization reactions was found to be active in the splitting of secondary amines to primary amines using NH3. Conversions up to 80% along with very high selectivities were achieved. However, after about 80% conversion the catalyst lost activity. Similar to Shvo's catalyst, the complex might deactivate under the influence of ammonia. It was revealed that not NH3 but mainly the primary amine is responsible for the deactivation.

Combined ruthenium(II) and lipase catalysis for efficient dynamic kinetic resolution of secondary alcohols. Insight into the racemization mechanism

Pentaphenylcyclopentadienyl ruthenium complexes (3) are excellent catalysts for the racemization of secondary alcohols at ambient temperature. The combination of this process with enzymatic resolution of the alcohols results in a highly efficient synthesis of enantiomerically pure acetates at room temperature with short reaction times for most substrates. This new reaction was applied to a wide range of functionalized alcohols including heteroaromatic alcohols, and for many of the latter, enantiopure acetates were efficiently prepared for the first time via dynamic kinetic resolution (DKR). Different substituted cyclopentadienyl ruthenium complexes were prepared and studied as catalysts for racemization of alcohols. Pentaaryl-substituted cyclopentadienyl complexes were found to be highly efficient catalysts for the racemization. Substitution of one of the aryl groups by an alkyl group considerably slows down the racemization process. A study of the racemization of (S)-1-phenylethanol catalyzed by ruthenium hydride η5-Ph5CpRu(CO) 2H (8) indicates that the racemization takes place within the coordination sphere of the ruthenium catalyst. This conclusion was supported by the lack of ketone exchange in the racemization of (S)-1-phenylethanol performed in the presence of p-tolyl methyl ketone (1 equiv), which gave 1% of 1-(p-tolyl)ethanol. The structures of ruthenium chloride and iodide complexes 3a and 3c and of ruthenium hydride complex 8 were confirmed by X-ray analysis.