20306-86-9Relevant articles and documents
Diazomethane Radical Cations as a Dipolarophile in the Dimeric Olefin Formation from Diazo-compounds
Ishiguro, Katsuya,Sawaki, Yasuhiko,Iwamura, Hiizu
, p. 1853 - 1856 (1987)
A novel cycloaddition mechanism involving diazomethane radical cations is proposed for the dimeric olefin formation by the one-electron oxidation of the diazo-compounds.The preference of cis-stilbene formation from phenyldiazomethane is understood by a secondary orbital interaction of phenyl groups on the cycloaddition step.
Lipase/palladium-catalyzed asymmetric transformations of ketoximes to optically active amines.
Choi,Kim,Ahn,Kim
, p. 4099 - 4101 (2001)
[reaction: see text] Prochiral ketoximes were asymmetrically transformed to optically active amines in the acetylated forms by coupled lipase/palladium catalysis in the presence of an acyl donor under 1 atm of hydrogen.
Biocatalytic, Intermolecular C?H Bond Functionalization for the Synthesis of Enantioenriched Amides
Arnold, Frances H.,Athavale, Soumitra V.,Gao, Shilong,Hirschi, Jennifer S.,Liu, Zhen,Mallojjala, Sharath Chandra
supporting information, p. 24864 - 24869 (2021/10/15)
Directed evolution of heme proteins has opened access to new-to-nature enzymatic activity that can be harnessed to tackle synthetic challenges. Among these, reactions resulting from active site iron-nitrenoid intermediates present a powerful strategy to forge C?N bonds with high site- and stereoselectivity. Here we report a biocatalytic, intermolecular benzylic C?H amidation reaction operating at mild and scalable conditions. With hydroxamate esters as nitrene precursors, feedstock aromatic compounds can be converted to chiral amides with excellent enantioselectivity (up to >99 % ee) and high yields (up to 87 %). Kinetic and computational analysis of the enzymatic reaction reveals rate-determining nitrenoid formation followed by stepwise hydrogen atom transfer-mediated C?H functionalization.
C-H Amination via Electrophotocatalytic Ritter-Type Reaction
Lambert, Tristan H.,Shen, Tao
supporting information, p. 8597 - 8602 (2021/06/28)
A method for C-H bond amination via an electrophotocatalytic Ritter-Type reaction is described. The reaction is catalyzed by a trisaminocyclopropenium (TAC) ion in an electrochemical cell under irradiation. These conditions convert benzylic C-H bonds to acetamides without the use of a stoichiometric chemical oxidant. A range of functionality is shown to be compatible with this transformation, and several complex substrates are demonstrated.
