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...
The copper(i)-promoted cross-coupling of 1,2-di(pyrimidin-2-yl) disulfides with aromatic amines and aliphatic amines to deliver C-N coupling products in moderate to good yields is reported in this paper. Central to this strategy is the conversion of disulfides into aryl- and alkyl amines by a copper-promoted chemoselective C-S bond cleavage.
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.
Nitrenoid-mediated C–H insertion and cycloaddition reactions are gaining increasing importance in modern organic synthesis. However, the nitrene-mediated benzene ring expansion, which constitutes a potent tool for breaking the benzene ring, has sparely been explored for synthetic purposes. Herein we report that nitrene cycloaddition to the benzene ring can be enabled intramolecularly by iron catalysis. By using FeCl2 and N-heterocyclic carbene SIPr HCl as the catalyst, α-azido-N-phenylamides can be converted to 1,3-dihydro-2H-azepin-2-ones in good yield through a novel skeleton rearrangement. The rearrangement features a cascade of nitrene cycloaddition, C–N cleavage, water addition and electrocyclic ring-opening. In case that the N-phenyl ring is substituted with a methoxy group at the meta or para position, azepin-2-one-fused imidazolinones can also be obtained. The present reactions provide an effective method for benzene ring expansion as well as for the preparation of azepin-2-one compounds.
Herein, we report a novel iron-catalyzed
skeleton rearrangement
of alkyl azides. Upon treatment with FeCl2 and N-heterocyclic
carbene SIPr·HCl in the presence of H2O and Et3N, 2-azido-N,N-diphenylamides
underwent 1,4-phenyl migration and ring expansion to give azepin-2-ones
in good yield. The reaction proceeds via intramolecular nitrene cycloaddition
followed by C–N cleavage, water addition, and electrocyclic
ring opening.
A metal-free synthesis of C2-functionalized pyrimidines via the reaction of pyrimidin-2-yl phosphates with amines and thiophenols in PEG-400 has been developed. The desired products can be generated in good to excellent yields in the environmentally friendly PEG-400, without any catalysts or other additives.
A CuTC-promoted C-N cross-coupling of 1,2-di(pyrimidin-2yl) disulfides with N-heterocyclic compounds including indoles, triazole benzotriazole, and benzoimidazole by C-S cleavage of the disulfides is reported.
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