4565-18-8Relevant academic research and scientific papers
O -Iodoxybenzoic acid mediated generation of aryl free radicals: Synthesis of stilbenes through C-C cross-coupling with β-nitrostyrenes
Wagh, Ganesh,Autade, Snehalata,Patil, Pravin C.,Akamanchi, Krishnacharya G.
, p. 3301 - 3309 (2018)
The generation of an aryl free radicals in the presence of nitrostyrenes through a combination of aryl hydrazines and o-iodoxybenzoic acid led to the synthesis of stilbenes by forming a new carbon-carbon bond after subsequent elimination of a nitrosyl radical. The symmetrical and unsymmetrical stilbenes with excellent E-selectivity were synthesized in good yields, with advantages of broad substrate scope and transition metal free, mild reaction conditions, under an open atmosphere in a short reaction time. A free radical mediated mechanism was postulated and supported by radical trapping experiments. Application of the developed methodology is demonstrated through a simple, two step synthesis of resveratrol, a valuable stilbenoid for anticancer and neurological studies via its prodrug E-1,3-dimethoxy-5-(4-methoxystyryl)benzene.
