Palladium-catalyzed carbonylation of o-iodoanilines for synthesis of isatoic anhydrides
A novel palladium-catalyzed oxidative double carbonylation of o-iodoanilines for the synthesis of isatoic anhydrides has been developed. The reaction employs readily available o-iodoanilines as the starting materials and proceeds under mild conditions. For extension, palladium-catalyzed oxidative carbonylation of anthranilic acids was developed for the synthesis of substituted isatoic anhydrides in high to excellent yields.
Palladium-catalyzed C-H bond carboxylation of acetanilides: An efficient usage of N,N-dimethyloxamic acid as the carboxylate source
N,N-Dimethyloxamic acid can be successfully employed as a carboxylate precursor in the palladium-catalyzed direct C-H carboxylation of acetanilides. The reaction proceeds smoothly under mild conditions over a broad range of substrates with high functional group tolerance, affording substituted N-acyl anthranilic acids in moderate to high yields.
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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