Glycosylated oligo(ethynylene)s via a Pd/Zn-mediated cross-coupling reaction

Abstract

The synthesis of higher oligo(ethynylene)s represents a challenge in modern organic chemistry, because of their decreasing stability with increasing length and side-product formation during the reaction. Recently, we reported the development of a mild and convenient sp-sp carbon heterocoupling protocol for the preparation of glycosylated oligo(ethynylene)s based on the Negishi reaction. The application of this protocol in combination with a one-step desilylation-bromination allowed for the sequential synthesis of glycosylated oligo(ethynylene)s up to the octayne. © Schweizerische Chemische Gesellschaft.