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Keywords:

  • Synthetic methods;
  • Arenes;
  • ­Imaging agents;
  • Sulfones;
  • Amides;
  • ­Olefination;
  • Grignard reaction

Abstract

In an effort to arrive at bis(styrylbenzene) derivatives, which are known for their importance in connection to Alzheimer's disease, two bifunctional building blocks that enable a C–C bond formation through a Julia–Kocienski reaction were synthesized. The orthogonal nature of the two functional groups in these building blocks allow the sequential olefination of commercially available aromatic aldehydes and the intermediate stilbene aldehydes to deliver an efficient and new route for bis(styrylbenzenes) with Weinreb amide (WA) functionality for the first time. The successful incorporation of the WA functionality has facilitated convenient access to unknown bis(styrylbenzenes) with acyl and formyl groups as substituents This strategy has also paved the way for highly functionalized bis(styrylbenzenes) with a tetrafluorophenyl core, which have potential as new contrast agents for MRI applications.