Huisgen cycloaddition has proven to be a powerful tool for the derivatization of cellulose, but the choice of reaction partners is limited by the solubility of the cellulose derivative. In this report, we show the efficient synthesis of an azide-bearing, organosoluble cellulose derivative via the 6-bromo-6-deoxy-2,3-O-trimethylsilyl cellulose (Br-TMSC) obtained through a novel one-pot reaction. It opens the possibility to perform the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) under moisture free conditions. First, the one-pot approach was used to synthesize Br-TMSC by combining homogeneous and regioselective bromination at C-6 position and silylation at C-2/C-3 positions. Then, 6-azido-6-deoxy-2,3-O-trimethylsilyl cellulose (N₃-TMSC) as the starting material for the CuAAC was obtained via nucleophilic substitution of the bromine by azide moiety. Furthermore, N₃-TMSC was exemplarily reacted with phenylacetylene and 3-cyclopentyl-1-propyne in the CuAAC in dry tetrahydrofuran (THF) as solvent and showed nearly complete conversion of the azide functionality. All products have been characterized by FTIR spectroscopy, NMR spectroscopy and elemental analysis.

已证明，Huisgen环加成是纤维素衍生化的强大工具，但反应伙伴的选择受到纤维素衍生物溶解度的限制。在此报告中，我们显示了通过新型一锅反应获得的6-溴-6-脱氧-2,3-O-三甲基甲硅烷基纤维素（Br-TMSC）可以有效合成含叠氮的有机可溶性纤维素衍生物。这为在无湿气条件下进行铜（I）催化的叠氮化物-炔烃环加成反应（CuAAC）开辟了可能性。首先，通过结合在C-6位的均相和区域选择性溴化以及在C-2 / C-3位的甲硅烷基化，采用一锅法合成Br-TMSC。然后，6-叠氮基-6-脱氧-2,3-O-三甲基甲硅烷基纤维素（N ₃通过叠氮化物部分对溴的亲核取代获得了作为CuAAC原料的-TMSC）。此外，在干燥的四氢呋喃（THF）中，在CuAAC中使N ₃ -TMSC示例性地与苯乙炔和3-环戊基-1-丙炔反应，并显示叠氮化物官能度几乎完全转化。所有产品均已通过FTIR光谱，NMR光谱和元素分析进行​​了表征。