671803-50-2Relevant academic research and scientific papers
Titration of nonstabilized diazoalkane solutions by fluorine NMR
Rendina, Victor L.,Kingsbury, Jason S.
experimental part, p. 1181 - 1185 (2012/03/12)
A new protocol for titrating nonstabilized diazoalkane solutions by quantitative 19F NMR is reported. An excess of 2-fluorobenzoic acid dissolved in CDCl3 is treated with the diazoalkane solution at a low temperature, immediately forming the corresponding 2-fluorobenzoate ester upon warming. A significant difference in the 19F chemical shift between the ester and acid is seen, allowing facile and accurate integration to determine titer. The procedure is safe, rapid, and indicates the active diazoalkane concentration with high precision.
An enantioselective synthesis of 2-aryl cycloalkanones by sc-catalyzed carbon insertion
Rendina, Victor L.,Moebius, David C.,Kingsbury, Jason S.
, p. 2004 - 2007 (2011/07/07)
Current methods for asymmetric α-arylation require blocking groups to prevent reaction at the R0-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.
