Facile amine formation by intermolecular catalytic amidation of carbon-hydrogen bonds
A simple copper-based catalytic system has been developed for the carbon-hydrogen amidation reaction. The copper-homoscorpionate complex Tp Br3Cu(NCMe) catalyzes the transfer of the nitrene unit NTs (Ts = p-toluenesulfonyl) and its subsequent insertion into the sp3 C-H bonds of alkyl aromatic and cyclic ethers or the sp2 C-H bonds of benzene using PhI=NTs as the nitrene source, affording the corresponding trisubstitued NR1HTs amines in moderate to high yields. The use of the environmentally friendly chloramine-T has also proven effective, with the advantage that sodium chloride is formed as the only byproduct. A tandem, one-pot consecutive nitrene-carbene insertion system has been developed to yield amino acid derivatives.
Fructos, Manuel R.,Trofimenko, Swiatoslaw,Mar Diaz-Requejo,Perez, Pedro J.
p. 11784 - 11791
(2007/10/03)
Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation
The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene (4 mol %) in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective.
Alonso, Emma,Ramon, Diego J.,Yus, Miguel
p. 14355 - 14368
(2007/10/03)
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