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Disproportionation of aliphatic and aromatic aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions

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Abstract

Disproportionation of aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions often requires the application of high temperatures, equimolar or excess quantities of strong bases, and is mostly limited to the aldehydes with no CH2 or CH3 adjacent to the carbonyl group. Herein, we developed an efficient, mild, and multifunctional catalytic system consisting AlCl3/Et3N in CH2Cl2, that can selectively convert a wide range of not only aliphatic, but also aromatic aldehydes to the corresponding alcohols, acids, and dimerized esters at room temperature, and in high yields, without formation of the side products that are generally observed. We have also shown that higher AlCl3 content favors the reaction towards Cannizzaro reaction, yet lower content favors Tishchenko reaction. Moreover, the presence of hydride donor alcohols in the reaction mixture completely directs the reaction towards the Meerwein–Ponndorf–Verley reaction.

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Acknowledgements

We are grateful to the financial support from Boston-KPro research fund.

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Authors and Affiliations

  1. Department of Chemistry, University of Connecticut, Storrs, CT, 06269, USA

    Sina Sharifi

  2. Disruptive Technology Laboratory, Schepens Eye Research Institute of Massachusetts Eye and Ear, Harvard Medical School, Boston, MA, 02114, USA

    Sina Sharifi & Hannah Sharifi

  3. Department of Science, Eastern Connecticut State University, Willimantic, CT, 06226, USA

    Darrell Koza

  4. Department of Chemistry, Khoy Branch, Islamic Azad University, 58168, Khoy, Iran

    Ali Aminkhani

Authors
  1. Sina Sharifi
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  2. Hannah Sharifi
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  3. Darrell Koza
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  4. Ali Aminkhani
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Correspondence to Sina Sharifi.

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Sharifi, S., Sharifi, H., Koza, D. et al. Disproportionation of aliphatic and aromatic aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions. Monatsh Chem 152, 803–808 (2021). https://doi.org/10.1007/s00706-021-02785-9

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  • DOI: https://doi.org/10.1007/s00706-021-02785-9

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