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N-Chlorosuccinimide (NCS)–N,N-dimethylformamide (DMF), a reagent for the oxidation of benzylic alcohols to aldehydes and ketones

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Abstract

The oxidation of benzylic alcohol to corresponding aldehyde and ketone using N-chlorosuccinimide (NCS)–N,N-dimethylformamide (DMF) has been described. This method gives easy access to the corresponding carbonyl compounds under metal-free conditions, without the use of corrosive reagent at ambient temperature in good yield.

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Scheme 1
Scheme 2
Fig. 1

aAt room temperature, the oxidation is not initiated; however, on heating to 50 °C for 16 h, 60–70% conversion was observed by TLC; the yield 0% no reaction initiation even on heating at 50 °C for 16 h (isolated back starting materials). In case of 2x, traces of product was confirmed by LC–MS, and the starting material was degraded under reaction conditions

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Acknowledgements

The authors are thankful to Dr. V. B. Gaikwad (Principal) K.R.T. Arts, B.H. Commerce and A.M. Science College, Gangapur Road, Nashik 422 002, MS, India, for continuous support and encouragement.

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Authors and Affiliations

  1. Organic Chemistry Research Centre, Department of Chemistry, K.R.T. Arts, B.H. Commerce and A.M. Science College, Gangapur Road, Nashik, MS, 422 002, India

    Mahesh R. Kulkarni, Nitin P. Lad & Nitin D. Gaikwad

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  1. Mahesh R. Kulkarni
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Correspondence to Nitin D. Gaikwad.

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Kulkarni, M.R., Lad, N.P. & Gaikwad, N.D. N-Chlorosuccinimide (NCS)–N,N-dimethylformamide (DMF), a reagent for the oxidation of benzylic alcohols to aldehydes and ketones. Mol Divers 24, 437–442 (2020). https://doi.org/10.1007/s11030-019-09954-3

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