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Molecules 2018, 23(12), 3163; https://doi.org/10.3390/molecules23123163

Mechanochemical Catalytic Transfer Hydrogenation of Aromatic Nitro Derivatives

Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
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Received: 15 November 2018 / Revised: 28 November 2018 / Accepted: 29 November 2018 / Published: 30 November 2018
(This article belongs to the Special Issue Recent Development of Mechanochemical Synthesis)
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Abstract

Mechanochemical ball milling catalytic transfer hydrogenation (CTH) of aromatic nitro compounds using readily available and cheap ammonium formate as the hydrogen source is demonstrated as a simple, facile and clean approach for the synthesis of substituted anilines and selected pharmaceutically relevant compounds. The scope of mechanochemical CTH is broad, as the reduction conditions tolerate various functionalities, for example nitro, amino, hydroxy, carbonyl, amide, urea, amino acid and heterocyclic. The presented methodology was also successfully integrated with other types of chemical reactions previously carried out mechanochemically, such as amide bond formation by coupling amines with acyl chlorides or anhydrides and click-type coupling reactions between amines and iso(thio)cyanates. In this way, we showed that active pharmaceutical ingredients Procainamide and Paracetamol could be synthesized from the respective nitro-precursors on milligram and gram scale in excellent isolated yields.
Keywords: mechanochemistry; catalytic transfer hydrogenation; aromatic nitro derivatives; ammonium formate; aging; ball milling; synthesis mechanochemistry; catalytic transfer hydrogenation; aromatic nitro derivatives; ammonium formate; aging; ball milling; synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Portada, T.; Margetić, D.; Štrukil, V. Mechanochemical Catalytic Transfer Hydrogenation of Aromatic Nitro Derivatives. Molecules 2018, 23, 3163.

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