α-Aminophosphonate derivatives of triethoxysilane for the synthesis of surface-modified silica

Abstract

A convenient synthetic route for the preparation of α-aminophosphonate derivatives of triethoxysilane, attractive precursors for silica surface functionalization, was developed. The condensation of commercially available APTES with carbonyl compounds followed by Pudovik reaction of imines with diethyl phosphite yielded desired N-phosphonomethyl functionalized (3-aminopropyl)triethoxysilanes in high yields without further purification. The chemical structures of obtained products were undoubtedly proved by ¹H, ¹³C and ³¹P NMR spectroscopy, elemental analysis and mass spectrometry.

Graphical Abstract

Keywords:

• 3-Aminopropyltriethoxysilane
• α-aminophosphonates
• Kabachnik-Fields reaction
• modified silica
• Pudovik reaction

Acknowledgments

We are grateful to V.I. Musatov (“Institute for Single Crystals” NAS of Ukraine, Kharkiv, Ukraine), Enamine Ltd. (Kiev, Ukraine) for spectroscopic measurements and Albina Mikhralieva (Rio de Janeiro, Brazil) for fruitful discussion.

Additional information

Funding

This work was supported by V.N. Karazin Kharkiv National University [Grant 811Н/12-17] and Ministry of Education and Science of Ukraine [Grant 0118U002025].