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

The Wittig reaction of perfluorohalobenzaldehydes was systematically studied to synthesize 2,3,5,6-tetrafluoro-4-halostyrene (TFXS) as functional monomers bearing halogen bond donor sites. The reaction proceeded efficiently in tetrahydrofuran using 1,1,3,3-tetramethylguanidine as the organic base. Correlation analysis quantitatively identified three key factors required to obtain TFXS 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.