Synthesis of d-glucose and l-phenylalanine substituted phenylene–thiophene oligomers

Phenylene–thiophene oligomers bearing peracetylated β-d-glucose or N-BOC-l-phenylalanine as chiral substituents were synthesized in good yields by a versatile protocol based on the Suzuki–Miyaura cross-coupling reaction. Aryl iodides bearing the chiral biomolecules as substituents efficiently reacted with pinacol boronates of bi- or terthiophenes leading to the bio-functionalized oligomers in good yields.

Graphical abstractA versatile synthetic approach to several phenylene–thiophene oligomers decorated with peracetylated β-D-glucose or N-BOC protected l-phenylalanine as chiral substituents is reported.Figure optionsDownload full-size imageDownload as PowerPoint slide