Synthesis of Aminobisphosphinates through a Cascade Reaction between Hypophosphorous Acid and Bis(trimethylsilyl)imidates Mediated by ZnI2

Nouha Ayadi; Aurélie Descamps; Thibaut Legigan; Jade Dussart-Gautheret; Maelle Monteil; Evelyne Migianu-Griffoni; Taïcir Ben Ayed; Julia Deschamp; Marc Lecouvey

doi:10.20944/preprints202308.0363.v1

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Ayadi, N.; Descamps, A.; Legigan, T.; Dussart-Gautheret, J.; Monteil, M.; Migianu-Griffoni, E.; Ben Ayed, T.; Deschamp, J.; Lecouvey, M. Synthesis of Aminobisphosphinates through a Cascade Reaction between Hypophosphorous Acid and Bis(trimethylsilyl)imidates Mediated by ZnI₂. Molecules 2023, 28, 6226. Ayadi, N.; Descamps, A.; Legigan, T.; Dussart-Gautheret, J.; Monteil, M.; Migianu-Griffoni, E.; Ben Ayed, T.; Deschamp, J.; Lecouvey, M. Synthesis of Aminobisphosphinates through a Cascade Reaction between Hypophosphorous Acid and Bis(trimethylsilyl)imidates Mediated by ZnI2. Molecules 2023, 28, 6226.

Abstract

Among phosphorylated derivatives, phosphinates occupy a prominent place due to their ability to be bioisosteres of phosphates and carboxylates. These properties imply the necessity to develop efficient methodologies leading to phosphinate scaffolds. For the past years our team have explored the nucleophilic potential of silylated phosphonite towards various electrophiles. In this paper, we propose to extend our study over other electrophiles. We describe here the implementation of a cascade reaction between (trimethylsilyl)imidates and hypophosphorous acid mediated by a Lewis acid allowing the synthesis of aminomethylenebisphosphinate derivatives.

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Synthesis of Aminobisphosphinates through a Cascade Reaction between Hypophosphorous Acid and Bis(trimethylsilyl)imidates Mediated by ZnI2

Abstract

Keywords

Subject

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Synthesis of Aminobisphosphinates through a Cascade Reaction between Hypophosphorous Acid and Bis(trimethylsilyl)imidates Mediated by ZnI₂