Electrochemical Fe-catalysed radical cyclization for the synthesis of oxindoles
Tianxiang Ren1, Ruina Qu1, Lu Song1
1Key Laboratory of Bio-Inspired Smart Interfacial Science and Technology of Ministry of Education, School of Chemistry, Beihang University, Beijing, China. songlu@buaa.edu.cn.
Abstract:
We report an efficient and sustainable electrocatalytic approach for the synthesis of 3,3-disubstituted 2-oxindoles bearing ester groups from readily accessible N-arylacrylamides and carbazates. The reaction proceeds through an electrochemical iron-catalyzed radical addition/cyclization sequence with a commercially available iron catalyst and carbazates as alkoxycarbonyl radical precursors. This mild and operationally simple method transforms a wide range of structurally diverse N-arylacrylamides into oxindole derivatives in good yields and can be smoothly scaled up for the preparation of synthetically valuable oxindoles that are key intermediates for the synthesis of natural products.
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