18435-75-1

Upstream product

• 294669-29-7 3-(2-hydroxyphenyl)cyclobutanone 
• 118-93-4 o-hydroxyacetophenone 
• 10277-93-7 2-isopropenylphenol 
• 1396690-36-0 2-(prop-1-en-2-yl)phenyl formate 
• 15243-33-1 dodecacarbonyl-triangulo-triruthenium 

Downstream Products

• 74181-02-5 2-[2-(1-Hydroxy-cyclopentyl)-1-methyl-ethyl]-phenol 
• 607-71-6 4-methyl-2H-chromen-2-one 
• 61073-14-1 2-(3-hydroxy-1-methylpropyl)phenol 
• 62191-63-3 3-(2-hydroxyphenyl)butyric acid 
• 61005-16-1 N-Methylcarbaminsaeure-o-(3-hydroxy-1-methylpropyl)-phenylester 
• 61073-17-4 3-(2-Methylcarbamoyloxy-phenyl)-butyric acid 
• 61005-11-6 3-(o-N-Methylcarbamoyloxyphenyl)buttersaeuremethylester 

Relevant academic research and scientific papers

Imidazole derivatives as accelerators for ruthenium-catalyzed hydroesterification and hydrocarbamoylation of alkenes: Extensive ligand screening and mechanistic study

Imidazole derivatives are effective ligands for promoting the [Ru3(CO)12]-catalyzed hydroesterification of alkenes using formates. Extensive ligand screening was performed to identify 2-hydroxymethylated imidazole as the optimal ligand. Neither carbon monoxide gas nor a directing group was required, and the reaction also showed a wide substrate generality. The Ru-imidazole catalyst system also promoted intramolecular hydrocarbamoylation to afford lactams. A Ru-imidazole complex was unambiguously analyzed by X-ray crystallography, and it had a trinuclear structure derived from one [Ru3(CO)12] and two ligands. This complex was also successfully used for hydroesterification. The mechanism was examined in detail by using D- and 13C-labeled formates, indicating that the hydroesterification reaction proceeds by a decarbonylation-recarbonylation pathway. Effective imidazole assistant: [Ru3(CO)12]-catalyzed hydroesterification of alkenes by using formates is drastically accelerated by imidazole derivatives and exhibits a broad substrate scope for both alkenes and formates. The Ru-imidazole complex also catalyzes the intramolecular hydrocarbamoylation of alkenes.

Remarkable improvement achieved by imidazole derivatives in ruthenium-catalyzed hydroesterification of alkenes using formates

Imidazole derivatives are revealed to be effective ligands in the Ru-catalyzed hydroesterification of alkenes using formates, affording one-carbonelongated esters in high yields. Further, intramolecular hydroesterification was successfully performed to give lactones for the first time. Imidazole derivatives can contribute to promote the reaction as well as to suppress the undesired decarbonylation of formate. Toxic CO gas, a directing group, and large excess alkenes are not required.

Lactone formation by rhodium-catalyzed C-C bond cleavage of cyclobutanone

As a coordinating ligand, the phenol group in appropriately substituted cyclobutanones facilitates the Rh1-catalyzed activation of the C-C bond between the carbonyl group and the α-carbon atom. This novel reaction leads, depending on the position of the phenol group on the cyclobutanone ring, to lactones of varying ring size (for example, as shown for a seven-membered-ring lactone).