Cu(II)-Mediated Ortho-C–H Amination of Arenes with Free Amines (original) (raw)
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Journal of the American Chemical Society, 2014
A Cu(OAc) 2-mediated C−H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and Nphenylaminobenzoates.
Journal of the American Chemical Society, 2016
Primary arylamines are an important unit broadly found in synthetic, biological, and materials science. Herein we describe the development of a (NHC)Cu system that mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A facile stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of (t)BuONa base made this transformation catalytic under mild conditions. The present (NHC)Cu-catalyzed C-H amidation works efficiently and selectively on a large scale over a range of arenes including polyfluorobenzenes, azoles, and quinoline N-oxides. Deprotection of the newly installed carbamate groups such as Boc and Cbz was readily performed to afford the corresponding primary arylamines.
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Angewandte Chemie International Edition, 2010
Alexander von Humboldt Foundation (re-invitation award to T.H.W.), and the Chemical Computing Group (MOE software to T.R.C.). Y.M.B. thanks Georgetown University for a Dissertation Fellowship and M.M.M. is grateful to the Luce Foundation for a predoctoral fellowship.
The Schiff base derived from 2-sulphanilamidopyridine and 2-hydroxy-3-methoxy benzaldehyde and its metal complexes have been synthesized and characterised by IR, 1 H NMR, UV, elemental analysis, molar conductance and magnetic susceptibility. The Schiff base ligand and the metal complexes were screened for antimicrobial activity by disc diffusion technique. From the analytical and spectral data, the stoichiometry has been found to be 1:2 for all the metal complexes. An octahedral structure has been proposed. All these metal complexes were found to be active against bacteria and fungi.
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A method for amination of aliphatic CÀH bonds of N-alkylamidines is described that utilizes Cu(OAc) 2 as the catalyst in the presence of PhI(OAc) 2 and K 3 PO 4. The resulting products, dihydroimidazoles and tetrahydropyrimidines, could be converted into the corresponding diamines by hydride reduction.
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Aromatic C-N bonds can be found in the chemical structures of many pharmaceuticals on the market today. Devising more direct synthetic routes to these functionalities could be highly beneficial to the pharmaceutical industry by making some syntheses more efficient than when approached from a classical organic standpoint. Most biologically