Fe(II)–phosphine
complex [Fe(dpbz)]Cl2 was demonstrated
to be effective for the intramolecular C(sp3)–H
amination of organic azides. This catalyst exhibited a high catalytic
capacity for the transformations from α-azido amides to imidazolinones.
Cyclization of simple aliphatic azides can be realized as well by
using [Fe(dpbz)]Cl2 as the catalyst.
Iron-catalyzed intramolecular C−H amination of aliphatic azides has recently emerged as a powerful tool for the preparation of nitrogen heterocycles. This paper reports that α-azidyl amides can be converted in high efficacy to imidazolinone compounds via intramolecular C(sp 3 )−H amination by the action of a simple catalytic system composed of FeCl 2 and a β-diketiminate ligand. The reactions provide a simple and atom-economical approach toward polysubstituted imidazolinones.
1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr HCl. The reaction generated aniline products in good yields after one-pot reduction...
This paper reports two new visible-light-promoted
radical reactions
of α-azido amides. By catalysis of [Ir(ppy)2(dtbbpy)]PF6 with i-Pr2NEt as the reducing
agent, N-aryl α-azido tertiary amides were
first converted to the corresponding aminyl radicals through reduction
of the azido group; the aminyl radicals then underwent N-to-N aryl
migration to give α-anilinyl-functionalized amides. α-Azido
secondary amides, on the other hand, reacted with the solvent ethanol
and i-Pr2NEt to afford the imidazolinone
products.
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