TfOH-Promoted Decyanative Cyclization toward the Synthesis of 2,1-Benzisoxazoles
A novel solvent-free, TfOH-promoted decyanative cyclization approach for the synthesis of 2,1-benzisoxazoles has been developed. The reactions are complete instantly at room temperature and result in the formation of the desired 2,1-benzisoxazoles in a 34-97% isolated yield.
Metal-Free, Visible-Light-Enabled Direct C3-H Arylation of Anthranils
An eosin Y disodium salt-catalyzed photoredox C-H arylation of anthranils is reported. A variety of aryl diazonium tetrafluoroborates were used as aryl sources, providing the C3 cross-coupled products. The in situ generated reactive radicals were trapped by anthranils, providing an alternative method to transition-metal-catalyzed C-H arylations of anthranils. Gold-catalyzed downstream transformations demonstrate the synthetic potential of these valuable building blocks.
Adak, Tapas,Hashmi, A. Stephen K.,Hu, Chao,Li, Jun,Rudolph, Matthias
supporting information
(2020/07/24)
Intramolecular Fe(II)-Catalyzed N-O or N-N bond formation from aryl azides
(Figure presented) Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.
Stokes, Benjamin J.,Vogel, Carl V.,Urnezis, Linda K.,Pan, Minjie,Driver, Tom G.
supporting information; experimental part
p. 2884 - 2887
(2010/08/21)
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