Abstract
The ball-milling process of ABB' Povarov reaction through mechano-chemical activation with phosphomolybdic acid (PMA) as heteropolyacid (HPA) catalyst, was first time explored. The developed high speed vibratory ball milling (HSVBM) green method offers simple and efficient diastereoselective synthesis of cis-2,4-disubstituted tetrahydroquinolines in good to excellent yields (56-76%).
Highlights
Several physical methods have been used to promote chemical reactions, including sonication, microwave, photocatalysis and the mechano-chemical approaches
Taking into account previous studies[15,16] and several different reaction parameters used to promote the imino DA reaction, including Lewis and Brønsted acids, we appointed towards the use of Brønsted acids
We used the polyethylene glycol 400 (PEG-400) as reaction medium with the phosphomolybdic acid (PMA)
Summary
Several physical methods have been used to promote chemical reactions, including sonication, microwave, photocatalysis and the mechano-chemical approaches. At the same time this process depends on the mill type, ball material (quantity and size), scale of the synthesis, frequency, reaction time and energy dissipation. In this sense, the activation energy necessary to initiate a chemical reaction is directly related to the amount of energy in the system, and could be provided by grinding, shearing or extrusion.[3] Of these three energy input ways, the grinding is the most useful technique which describes the mechanical action by hard surfaces and could be make it through manual or ball-milling method. It should be noted that the mechano-chemical methodology has not been widely applied to promote the imino Diels-Alder (DA) reaction[4] and remains as a great challenge in the organic synthesis field
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