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Continuous-Flow Meerwein Arylation

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Abstract

The continuous-flow Meerwein arylation is demonstrated for a set of few aryl donors (anilines and m-amino-acetophenone) and specific radical acceptors. Homogeneous catalyst (CuBr in HBr and CuCl in HCl) was used to facilitate the reaction. The effect of parameters, viz., temperature, catalyst concentration, residence time, and concentration of the radical acceptor on the yield of the arylated product, was studied. The yield of the aryl derivative obtained by continuous-flow syntheses was always better than the respective experiments in batch mode. Flow synthesis allows easy variation in these parameters and thus allows going close to the maximum possible yields in a system where the relative rates of different reactions create a complex situation. Temperature plays a crucial role by affecting the rates as well as by governing the system homogeneity. The nitrogen bubbles generated in the reaction helped to avoid any channel blockage.

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Authors and Affiliations

  1. Chem. Eng. & Proc. Dev. Div., CSIR-National Chemical Laboratory, Pune, India

    Vinay G. Bhaya & Amol A. Kulkarni

  2. Organic Chemistry Division, CSIR-National Chemical Laboratory, Pune, India

    Ramesh A. Joshi

Authors
  1. Vinay G. Bhaya
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  2. Ramesh A. Joshi
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  3. Amol A. Kulkarni
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Correspondence to Amol A. Kulkarni.

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Bhaya, V.G., Joshi, R.A. & Kulkarni, A.A. Continuous-Flow Meerwein Arylation. J Flow Chem 4, 211–216 (2014). https://doi.org/10.1556/JFC-D-14-00023

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  • DOI: https://doi.org/10.1556/JFC-D-14-00023

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