Synthesis of a novel resorcin[4]arene-glucose conjugate and its catalysis of the CuAAC reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles in water

Ali A Husain; Kirpal S Bisht

doi:10.1039/c9ra00972h

Synthesis of a novel resorcin[4]arene-glucose conjugate and its catalysis of the CuAAC reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles in water

RSC Adv. 2019 Mar 29;9(18):10109-10116. doi: 10.1039/c9ra00972h. eCollection 2019 Mar 28.

Authors

Ali A Husain¹, Kirpal S Bisht¹

Affiliation

¹ Department of Chemistry, University of South Florida 4202 East Fowler Avenue, CHE 205 Tampa FL 33620 USA kbisht@usf.edu.

Abstract

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.