Mechanochemical Catalytic Transfer Hydrogenation of Aromatic Nitro Derivatives

Portada, Tomislav; Margetić, Davor; Štrukil, Vjekoslav (2018) Mechanochemical Catalytic Transfer Hydrogenation of Aromatic Nitro Derivatives. Molecules, 23 (12). ISSN 1420-3049

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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.

Item Type:	Article
Uncontrolled Keywords:	mechanochemistry ; catalytic transfer hydrogenation ; aromatic nitro derivatives ; ammonium formate ; aging ; ball milling ; synthesis
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Nekovalentne interakcije u dizajnu novih fotoosjetljivih molekula-NoncoPhoto Davor Margetić IP-2013-11-9310 HRZZ
Depositing User:	Vjekoslav Štrukil
Date Deposited:	11 Jun 2019 12:21
URI:	http://fulir.irb.hr/id/eprint/4542
DOI:	10.3390/molecules23123163

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