Synthesis of Halogen-Bond-Donor-Site-Introduced Functional Monomers through Wittig Reaction of Perfluorohalogenated Benzaldehydes: Toward Digitalization as Reliable Strategy in Small-Molecule Synthesis

Tatsuaki Hori, Shuya Kakinuma, Naoya Ohtsuka, Takeshi Fujinami, Toshiyasu Suzuki, Norie Momiyama

The Wittig reaction of perfluoromonohalobenzaldehydes was systematically studied to synthesize 2,3,5,6-tetrafluoro-4-halostyrene (TFXSs) as functional monomers bearing halogen-bond donor sites. The reaction proceeded efficiently in tetrahydrofuran using 1,1,3,3-tetramethylguanidine as an organic base. Correlation analysis quantitatively identified three key factors required to obtain TFXSs in reasonable yields. The present approach not only contributes to the study of halogen-bond-based functional molecules, but also presents digitalization as a potential strategy in small-molecule synthesis.
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