Biaryl Peptides from 4-Iodophenylalanine by Solid-Phase Borylation and Suzuki-Miyaura Cross-Coupling

Resin‐bound phenylalanine boronates were prepared by solid‐phase Miyaura borylation of 4‐iodophenylalanine peptides. Subsequent arylation through a Suzuki–Miyaura cross‐coupling was carried out using a variety of aryl halides under conventional heating and under microwave irradiation. Microwaves greatly enhanced the arylation, shortening thereaction time and providing the biaryl peptides in higherpurities. A convenient strategy for the modification of phenylalanine peptides through solid‐phase borylation and subsequent cross‐coupling was developed. This methodology yielded resin‐bound phenylalanine boronates in good purities. Moreover, the cross‐coupling between a polymer‐bound phenylalanine boronate with different aryl halides led to a set of 4‐arylphenylalanine tripeptides.