Synthesis and CuAAC Reactions of Azidoalkylethoxysilanes: Grafting CuAAC Products onto Silica Surface

Abstract

One-pot synthetic protocols of novel azido functionalized silane coupling agents from corresponding terminal mesylated or tosylated 1-olefins were developed. Azido groups were successfully converted to the corresponding 1,2,3-triazol ring by the copper-catalyzed azido alkyne coupling (CuAAC) reaction without alkoxysilane decomposition. The CuAAC product was readily grafted onto the silica surface in good yield.

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GRAPHICAL ABSTRACT

Keywords:

• Azide
• CuAAC reaction
• silane coupling agent
• surface modification

ACKNOWLEDGMENTS

This work was carried out as a part of the Development of Microspace and Nanospace Reaction Environment Technology for Functional Materials Project under NEDO. The authors are grateful to R. Nagahata (AIST) and T. Yokoyama (MCPT) for the HRMS (ESI) measurement and nitrogen porosimetry analysis.