- Bond-Weakening Catalysis: Conjugate Aminations Enabled by the Soft Homolysis of Strong N-H Bonds
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The ability of redox-active metal centers to weaken the bonds in associated ligands is well precedented, but has rarely been utilized as a mechanism of substrate activation in catalysis. Here we describe a catalytic bond-weakening protocol for conjugate a
- Tarantino, Kyle T.,Miller, David C.,Callon, Ted A.,Knowles, Robert R.
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supporting information
p. 6440 - 6443
(2015/06/08)
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- Curtius rearrangement of aromatic carboxylic acids to access protected anilines and aromatic ureas
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(Diagram presented) The reaction of a chloroformate or di-tert-butyl dicarbonate and sodium azide with an aromatic carboxylic acid produces the corresponding acyl azide, presumably through the formation of an azidoformate. The acyl azide undergoes a Curtius rearrangement to form an isocyanate derivative which is trapped either by an alkoxide or by an amine to form the aromatic carbamate or urea. The reaction conditions are compatible with a variety of functional groups and allow the synthesis of a number of aniline derivatives containing alkyl, halide, nitro, ketone, ether, and thioether substituents.
- Lebel, Helene,Leogane, Olivier
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p. 5717 - 5720
(2007/10/03)
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