Synthesis of a 2,2'-Bipyridyl Functionalized Oligovinylene-Phenylene Using Heck and Horner-Wadsworth-Emmons Reactions and X-ray Crystal Structure of <em>E</em>-(4-(4-Bromostyryl)phenyl)(methyl)sulfane

Abstract

The synthesis of a new 2,2'-bipyridyl functionalized oligovinylenephenylene (<strong>OVP-5</strong>) containing a methyl protected thiol using Heck coupling and the Horner-Wadsworth-Emmons reaction and is described. A key step involving a diisopropylcarbodiimide promoted dehydration of a stable b-hydroxyphosphonate intermediate was identified. The structure of precursor <em>E</em>-(4-(4-bromostyryl)phenyl)(methyl)sulfane (<strong>1</strong>) was determined using X-ray crystallography.

Keywords

• oligovinylphenylene
• HWE reaction
• Heck coupling