Facile Amine Formation by Intermolecular Catalytic Amidation of Carbon−Hydrogen Bonds

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 TpBr3Cu(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 cyc...

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Veröffentlicht in:Journal of the American Chemical Society 2006-09, Vol.128 (36), p.11784-11791
Hauptverfasser: Fructos, Manuel R, Trofimenko, Swiatoslaw, Díaz-Requejo, M. Mar, Pérez, Pedro J
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General and physical chemistry
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container_end_page 11791
container_issue 36
container_start_page 11784
container_title Journal of the American Chemical Society
container_volume 128
creator Fructos, Manuel R
Trofimenko, Swiatoslaw
Díaz-Requejo, M. Mar
Pérez, Pedro J
description A simple copper-based catalytic system has been developed for the carbon−hydrogen amidation reaction. The copper−homoscorpionate complex TpBr3Cu(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.
doi_str_mv 10.1021/ja0627850
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General and physical chemistry
title Facile Amine Formation by Intermolecular Catalytic Amidation of Carbon−Hydrogen Bonds
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