Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of α-aminophosphonates via Kabachnik–Fields reaction under solvent-free condition

“…with ZrCl 4 ), solvent-free [ e.g . with Cp 2 Zr(OSO 2 C 4 F 9 ) 2 ·2H 2 O, ZrOCl 2 · 8H 2 O, or ZrO(ClO 4 ) 2 · 6H 2 O] or by grinding over Zr-supported pillared clay …”

Section: Resultsmentioning

confidence: 99%

“…Additionally, in the case of a possible metal-mediated process involving the milling media, the jar can be considered as a recyclable catalyst, with the advantage of not being responsible for metal-waste production, expanding the reactivity windows for heterogeneous KF-3CR. In this regard, zirconium- 58 or other metal-mediated synthesis of imine cannot be excluded, the process possibly occurring on the jar/balls surface.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Therefore, ball-milling the reactants in ZrO 2 jars represents a sustainable alternative to classic heterogenous catalysis making use of Lewis acids in solution (water-sensitive or not), the 'Zr source' being indefinitely recyclable and not producing any metal-waste, expanding the reactivity windows for heterogeneous KF-3CR. In this regard, zirconium-mediated synthesis of imine cannot be excluded, 58 the process occurring on the jar/balls surface.…”

mentioning

confidence: 99%

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

Fiore

Sović

Lukin

et al. 2020

ACS Sustainable Chem. Eng.

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-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 -aminophosphonate derivatives in high yields and with full selectivity, outperforming comparable solution procedures. The reaction is a Lewis acid-catalysed process occurring however without the addition of any external catalyst, but occurring on the surface of the zirconium oxide used as the milling media. The mechanism of the mechanochemical reaction was also investigated by in situ Raman spectroscopy, the kinetic behavior was disclosed. The solid-state structures of two representative compounds have been determined by single-crystal X-ray diffractions.

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“…[4][5][6][7] Numerous methods were described for the synthesis of a-aminophosphonates, however, the major part of the protocols reported applied a catalyst. [8][9][10][11][12][13][14][15][16] The senior author of this article, together with a coworker, was who proposed that using the microwave (MW)assisted solvent-free protocol, there is no need for any catalyst. [17] Hence, cost and environmental burdens may be saved.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of α-aminophosphine oxides by the Kabachnik-Fields reaction applying amides as the starting materials

Tripolszky

Zoboki

Bálint

et al. 2019

Synthetic Communications

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A series of acylated a-aminophosphine oxides were synthesized by the microwave-assisted Kabachnik-Fields reaction of a series of carboxylic acid amides, formaldehyde and secondary phosphine oxides. To compensate the lower reactivity of the-NH 2 reagents, they had to be used in an excess. The solvolytic condensations furnished the a-aminophosphine oxides in yields of 58-93% after purification by chromatography.

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Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of α-aminophosphonates via Kabachnik–Fields reaction under solvent-free condition

Cited by 32 publications

References 33 publications

A sustainable approach to synthesize phosphonated chitosan using ball milling and its application for oilfield scale management

A sustainable approach to synthesize phosphonated chitosan using ball milling and its application for oilfield scale management

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

Microwave-assisted synthesis of α-aminophosphine oxides by the Kabachnik-Fields reaction applying amides as the starting materials

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