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Recyclable cooperative catalyst for accelerated hydroaminomethylation of hindered amines in a continuous segmented flow reactor

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  • Malek Y. S. Ibrahim

    (North Carolina State University)

  • Milad Abolhasani

    (North Carolina State University)

Abstract

Synthesis of hindered amines using the atom-efficient hydroaminomethylation (HAM) route remains a challenge. Here, we report a general and accelerated HAM in segmented flow, achieved via a cooperative effect between rhodium (Rh)/N-Xantphos and a co-catalyst (2-Fluoro-4-methylbenzoic acid) to increase the reactivity by 70 fold when compared to Rh/Xantphos in batch reactors. The cooperation between Rh and the co-catalyst facilitates the cleavage of the H–H bond and drives the equilibrium-limited condensation step forward. Online reaction optimization expands the scope to include alkyl, aryl, and primary amines. In-flow solvent tuning enables selectivity switching from amine to enamine without the need for changing the ligand. Furthermore, leveraging the ionic nature of the catalyst, we present a robust Rh recovery strategy up to 4 recycles without loss of activity.

Suggested Citation

  • Malek Y. S. Ibrahim & Milad Abolhasani, 2022. "Recyclable cooperative catalyst for accelerated hydroaminomethylation of hindered amines in a continuous segmented flow reactor," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30175-0
    DOI: 10.1038/s41467-022-30175-0
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    1. Robert W. Pipal & Kenneth T. Stout & Patricia Z. Musacchio & Sumei Ren & Thomas J. A. Graham & Stefan Verhoog & Liza Gantert & Talakad G. Lohith & Alexander Schmitz & Hsiaoju S. Lee & David Hesk & Eri, 2021. "Metallaphotoredox aryl and alkyl radiomethylation for PET ligand discovery," Nature, Nature, vol. 589(7843), pages 542-547, January.
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