Glycosylated Oligo(ethynylene)s via a Pd/Zn-Mediated Cross-Coupling Reaction

Authors

  • Tobias N. Hoheisel
  • Holger Frauenrath

DOI:

https://doi.org/10.2533/chimia.2009.208

Keywords:

Carbon materials, Carbon-rich amphiphiles, Negishi cross-coupling, Oligo(ethynylene)s, Oligoynes

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 allowedfor the sequential synthesis of glycosylated oligo(ethynylene)s up to the octayne.

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Published

2009-04-29

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