“…To probe whether established reactive organonitrogen species are intermediates in the aminations catalyzed by 1 , a Diels−Alder trapping test for the intermediacy of free PhNO was found to be negative, with only allylic amines detected as products (eq 2). Likewise, the intervention of free aryl nitrene was excluded based on the absence of carbazole in the amination of AMS by o -nitrobiphenyl (eq 3). …”
The major iron-containing species present during and after the [Cp*Fe(CO) 2 ] 2 -catalyzed allylic amination of olefins by nitrobenzene is a novel cyclic carbamoyl complex 2. Complex 2 is found to be a resting state in the catalytic reaction.
“…To probe whether established reactive organonitrogen species are intermediates in the aminations catalyzed by 1 , a Diels−Alder trapping test for the intermediacy of free PhNO was found to be negative, with only allylic amines detected as products (eq 2). Likewise, the intervention of free aryl nitrene was excluded based on the absence of carbazole in the amination of AMS by o -nitrobiphenyl (eq 3). …”
The major iron-containing species present during and after the [Cp*Fe(CO) 2 ] 2 -catalyzed allylic amination of olefins by nitrobenzene is a novel cyclic carbamoyl complex 2. Complex 2 is found to be a resting state in the catalytic reaction.
“…(3)], but no detectable carbazole, the established product of intramolecular nitrene trapping. 14 Together these results suggest that a coordinated organonitrogen species serves as the active aminating agent in the reactions catalyzed by 1.…”
CpFe(CO) 2 ] 2 catalyzes the reaction of nitroaromatics with olefins under CO to produce allyl amines regioselectively; a coordinated organonitrogen species is implicated as the active aminating agent.
“…With yields of approximately 30%, 11 c and 11 d are the main products of this reaction. Since the Cadogan reaction occurs via stepwise deoxygenation of the nitro group, a nitrene is a possible intermediate …”
Dedicated to the memory of Prof. Dr. Helmut Bönnemann Suzuki-Miyaura-couplings to aryl-nitropyridines followed by Cadogan reactions is a straight-forward method for the synthesis of d-and b-carbolines. Microwave irradiation of the nitrobiaryls in triethyl phosphite solutions conveniently gives moderate to very good yields of the carbolines. Reduction to the amines without cyclization occurs on certain substrates, and alkylation of the products is observed as a follow-up reaction. Instead of a-carbolines, naphthonitriles are generated by phosphite reduction and ring transformation.
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