Synthesis of a novel resorcinarene–glucose conjugate and its catalysis of the CuAAC reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles in water†
The Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) in aqueous media using resorcinarene glycoconjugate (RG) is reported. The eight β-D-glucopyranoside moieties constructed on the resorcinarene 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.