15814-45-6Relevant articles and documents
In situ synthesis of 2-allyloxy-1-methylpyridinium triflate for the allylation of carboxylic acids
Strayer, Timothy A.,Culy, Caleb C.,Bunner, Matthew H.,Frank, Amie R.,Albiniak, Philip A.
, p. 6807 - 6809 (2015)
2-Allyloxypyridinium triflate is formed in situ by treating a mixture of 2-allyloxypyridine, a carboxylic acid, and toluene with methyl triflate. Subsequent warming of the reaction mixture in the presence of potassium carbonate leads to efficient formation of allyl esters in good to excellent yields.
Imidazolium Based Fluorous N-Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification
?ervenková ??astná, Lucie,Bílková, Veronika,Cézová, Tereza,Cu?ínová, Petra,Karban, Jind?ich,?ermák, Jan,Krupková, Alena,Stra?ák, Tomá?
, p. 3591 - 3598 (2020/06/17)
A series of new highly fluorophilic ionic liquids (f > 110) was synthetized from 3-iodopropyltris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane and N-alkyl imidazoles, followed by anion exchange. N-heterocyclic carbenes generated in situ from obtained imidazolium salts were employed to catalyze redox esterification (umpolung) of cinnamaldehyde with alcohols. The most effective N-methyl derivative with iodide as a counter anion was studied in detail with respect to the optimization of reaction conditions, substrate scope and recyclability. Recovery of the precatalyst was achieved using either fluorous extraction or performing the reaction in suitable fluorous biphase system with direct recycling of the fluorinated precatalyst phase. For both tested options, the catalytic activity did not significantly decrease within 5 subsequent cycles. The redox esterification was shown to proceed also in supercritical carbon dioxide (scCO2) as an alternative solvent where the activity of the fluorinated catalyst was also superior to the nonfluorinated model, while retaining the benefit of easy recycling.
Cobalt(II)-Catalyzed Alkoxycarbonylation of Aliphatic Amines via C-N Bond Activation
Li, Chong-Liang,Jiang, Xuan,Lu, Liang-Qiu,Xiao, Wen-Jing,Wu, Xiao-Feng
, p. 6919 - 6923 (2019/09/07)
The first cobalt-catalyzed deaminative alkoxycarbonylation reaction was described for the conversion of readily available primary alkyl amines to synthetically versatile esters with moderate to high yields. This transformation shows good functional group compatibility and can serve as a powerful tool for the modification of alkyl amine-containing complex natural products and drug molecules.
