Abstract
Huisgen’s [3+2] cycloaddition reaction was adapted to the functionalization of silica surface. Azido-modified silica gel 2 was prepared by mixing HPLC-grade silica and 3-azidopropyl triethoxysilane (1). The azido-silica 2 was treated with benzyl propargyl ether in the presence of CuSO4 at room temperature in aq EtOH to give silica gel beads 3a bearing a benzyloxymethyl triazole group. Silica beads 3b-d were also prepared from the corresponding terminal alkynes using a similar procedure. The resulting silica was filled into a HPLC column (F = 4.6 mm) to afford a ‘click’-functionalized HPLC packing. The click HPLC of hydroxymethyl 3d was tested with a small set of mono- and disaccharides (glucose, fructose, sucrose, and maltose).
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