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Graphene oxide-catalyzed two-step continuous-flow conversion of aryl amine to unsymmetrical thioether

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Abstract

A sustainable continuous-flow protocol for the conversion of aryl amine to unsymmetrical thioether is described. This technique is a two-step process involving graphene oxide (GO) catalyzed diazotization followed by the reaction with aryl/alkyl thiols. The continuous-flow conditions afford the desired thioethers in very good yields, effectively suppressing formation of possible disulfide, a common by-product in conventional process. The flow reaction is carried out under ambient conditions, applied to a variety of aryl amines and aryl/alkyl thiols and found to be scalable. The catalytic activity of the GO bed under continuous-flow conditions is found within standard time range and recyclable for ten consecutive runs without any loss of its performance.

Continuous-flow technique is applied in graphene oxide (GO) catalyzed conversion of aryl amine to unsymmetrical thioethers.

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Acknowledgements

Financial support from Science and Engineering Research Board (Grant No EMR/2015/000549), New Delhi, is gratefully acknowledged. PC thanks UGC, New Delhi, for Senior Research Fellowship under UGC–NET.

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Authors and Affiliations

  1. Department of Chemistry, North Bengal University, Darjeeling, 734013, India

    Prasun Choudhury & Basudeb Basu

  2. Department of Chemistry, Raiganj University, Raiganj, 733134, India

    Basudeb Basu

Authors
  1. Prasun Choudhury
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  2. Basudeb Basu
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Correspondence to Basudeb Basu.

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Article Highlights

• Graphene oxide (GO) catalysis in flow reaction.

• A metal-free continuous-flow synthesis of thioethers.

• The catalytic bed of GO is recyclable for ten cycles.

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Choudhury, P., Basu, B. Graphene oxide-catalyzed two-step continuous-flow conversion of aryl amine to unsymmetrical thioether. J Flow Chem 10, 389–396 (2020). https://doi.org/10.1007/s41981-019-00048-7

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  • DOI: https://doi.org/10.1007/s41981-019-00048-7

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