Husain Ali A, Bisht Kirpal S
Department of Chemistry, University of South Florida 4202 East Fowler Avenue, CHE 205 Tampa FL 33620 USA
RSC Adv. 2019 Mar 29;9(18):10109-10116. doi: 10.1039/c9ra00972h. eCollection 2019 Mar 28.
The Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) in aqueous media using resorcin[4]arene glycoconjugate (RG) is reported. The eight β-d-glucopyranoside moieties constructed on the resorcin[4]arene upper rim provide a pseudo-saccharide cavity that offers a suitable host environment for water-insoluble hydrophobic azido and/or alkyne substrates in water. The utility of RG was established as an efficient inverse phase transfer catalyst for the CuAAC in water as a green approach for the synthesis of 1,4-disubstituted 1,2,3-triazole species. The catalytic utility of RG (1 mol%) was demonstrated in a multicomponent one-pot CuAAC for various azido/alkyne substrates. The RG acts as a molecular host and a micro-reactor resulting in the 1,4-disubstituted 1,2,3-triazoles in excellent yield.
报道了使用间苯二酚[4]芳烃糖缀合物（RG）在水性介质中进行的铜（I）催化的叠氮化物-炔烃环加成反应（CuAAC）。在间苯二酚[4]芳烃上缘构建的八个β-D-吡喃葡萄糖苷部分提供了一个假糖腔，该腔为水中不溶性疏水叠氮基和/或炔烃底物提供了合适的主体环境。RG作为水中CuAAC的高效反相转移催化剂的效用得以确立，这是一种合成1,4-二取代1,2,3-三唑类化合物的绿色方法。RG（1 mol%）的催化效用在多组分一锅法CuAAC中针对各种叠氮基/炔烃底物得到了证明。RG充当分子主体和微反应器，以优异的产率得到1,4-二取代1,2,3-三唑。
