Beller, Matthias; Magerlein, Wolfgang; Indolese, Adriano F.; Fischer, Christine published the artcile< Efficient palladium-catalyzed alkoxycarbonylation of N-heteroaryl chlorides - A practical synthesis of building blocks for pharmaceuticals and herbicides>, Formula: C6H6ClNO, the main research area is butyl pyridinecarboxylate preparation; heteroaryl chloride alkoxycarbonylation palladium phosphine ligand catalyst; alkoxycarbonylation chloropyridine palladium catalyst.
The alkoxycarbonylation of various N-heteroaryl chlorides was examined in detail. Studies of the butoxycarbonylation of 2- and 3-chloropyridine revealed the importance of selecting both the right phosphine ligand and ligand concentration in order to obtain efficient conversion and selectivity. Amongst the different ligands tested, 1,4-bis(diphenylphosphino)butane (dppb) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) led to the most efficient palladium catalyst systems for the conversion of 2- and 4-chloropyridines and similar heteroaryl chlorides. For e.g., Bu pyridine-2-carboxylate was prepared in 95% yield in the presence of dppf ligand. The best catalytic systems for the alkoxycarbonylation of less activated substrates, such as 3-chloropyridines, were found to be those containing 1,4-bis(dicyclohexylphosphino)butane. Good to excellent yields of a number of N-heterocyclic carboxylic acid esters were realized by applying the appropriate ligand in the right concentration at low catalyst loadings (0.005-0.5 mol% Pd). For the first time catalyst turnover numbers (TON) of up to 13,000 were obtained for the carbonylation of a (hetero)aryl chloride.
Synthesis published new progress about Alkoxycarbonylation. 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Formula: C6H6ClNO.