Kabachnik–Fields Reaction by Mechanochemistry: New Horizons from Old Methods

Fiore, Cecilia; Sović, Irena; Lukin, Stipe; Halasz, Ivan; Martina, Katia; Delogu, Francesco; Ricci, Pier Carlo; Porcheddu, Andrea; Shemchuk, Oleksii; Braga, Dario; Pirat, Jean-Luc; Virieux, David; Colacino, Evelina (2020) Kabachnik–Fields Reaction by Mechanochemistry: New Horizons from Old Methods. ACS Sustainable Chemistry & Engineering, 8 (51). pp. 18889-18902. ISSN 2168-0485

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Abstract

α-Aminophosphonates are an important class of biologically active compounds, attracting considerable attention in medicinal chemistry, by inhibiting enzymes involved in amino acid metabolism. Herein, the Kabachnik–Fields domino reaction was investigated by mechanochemistry for the first-time preparation of α- aminophosphonate derivatives in high yields and with full selectivity, outperforming comparable solution procedures. The reaction occurs without the addition of any external catalyst, possibly via a metal-mediated process occurring on the surface of the jar (zirconium oxide was used as the milling media). The mechanism of the mechanochemical reaction was also investigated by in situ Raman spectroscopy, and the kinetic behavior was disclosed. The solid- state structures of two representative compounds have been determined by single- crystal X-ray diffraction.

Item Type:	Article
Uncontrolled Keywords:	Oxides ; Addition reactions ; Chemical reactions ; Ethyl groups ; Nuclear magnetic resonance spectroscopy
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Physical Chemistry
Depositing User:	Stipe Lukin
Date Deposited:	08 Dec 2021 14:17
URI:	http://fulir.irb.hr/id/eprint/6800
DOI:	10.1021/acssuschemeng.0c05744

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