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Cu(I) mediated hydrogen borrowing strategy for the α-alkylation of aryl ketones with aryl alcohols

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Abstract

New triazolium Schiff bases (TSBs) were synthesised via a simple and high throughput process. The new salts were successfully characterised. When reacted with Cu(CH3CN)4PF6, the TSB salts formed mononuclear triazole Schiff base copper(I) complexes and dinuclear complexes that were also characterised. The copper complexes were generated in situ (mixtures of TSB salts with Cu(CH3CN)4PF6) and applied as homogeneous catalysts for the C–C coupling of a variety of aryl ketones with aryl alcohols, from which significant reactivity was observed. Reaction conditions were optimised, and the results indicate that the catalyst systems are very robust. A catalyst concentration of 10 mol% efficiently and selectively catalysed the α-alkylation of methyl phenyl ketone and its derivatives to afford up to 94% yield of 1,3-diphenylpropan-1-one and its analogues. The process is adaptable with analogues of acetophenone and benzyl alcohol bearing various regulating substituents tolerated.

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Acknowledgements

We acknowledge financial support from the University of KwaZulu-Natal, ESKOM (TESP 2019) and the NRF. NSL thanks Ahmadu Bello University for a paid study fellowship.

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Authors and Affiliations

  1. School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban, 4000, South Africa

    Nasir S. Lawal, Halliru Ibrahim & Muhammad D. Bala

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  1. Nasir S. Lawal
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  2. Halliru Ibrahim
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  3. Muhammad D. Bala
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Correspondence to Muhammad D. Bala.

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Lawal, N.S., Ibrahim, H. & Bala, M.D. Cu(I) mediated hydrogen borrowing strategy for the α-alkylation of aryl ketones with aryl alcohols. Monatsh Chem 152, 275–285 (2021). https://doi.org/10.1007/s00706-021-02735-5

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  • DOI: https://doi.org/10.1007/s00706-021-02735-5

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