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Chemoselective Henry reaction catalyzed by electro-generated base

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Abstract

Chemoselective synthesis of 2-nitroalkanols catalyzed by electro-generated base (EGBs) in the presence of acetonitrile and lithium perchlorate has been studied by cyclic voltammetry and controlled potential electrolysis techniques. Cathodic reduction of nitromethane at platinum cathode produces organic anion which acts as EGBs and undergoes condensation with carbonyl group of substituted aldehydic substrate to produce 2-nitroalkanols in 75–85 % yields. The controlled nucleophilicity of EGBs in organic solvent during electrochemical reaction makes it chemoselective which is a unique feature of this work.

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Acknowledgments

The authors are grateful to the Head, Department of Chemistry and University of Allahabad for providing necessary facilities, SAIF Chandigarh for recording the 1H-NMR and 13C-NMR analysis, and UGC, New Delhi, India, for financial support.

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Authors and Affiliations

  1. Electrochemical Laboratory of Green Synthesis, Department of Chemistry, University of Allahabad, Allahabad, 211002, Uttar Pradesh, India

    A. Saraswat, L. K. Sharma, S. Singh, I. R. Siddiqui & R. K. P. Singh

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  1. A. Saraswat
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  2. L. K. Sharma
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  3. S. Singh
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  4. I. R. Siddiqui
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Correspondence to R. K. P. Singh.

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Saraswat, A., Sharma, L.K., Singh, S. et al. Chemoselective Henry reaction catalyzed by electro-generated base. Res Chem Intermed 39, 1393–1399 (2013). https://doi.org/10.1007/s11164-012-0695-6

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  • DOI: https://doi.org/10.1007/s11164-012-0695-6

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