Expanding the diversity of polycyclic aromatics through a Suzuki-Miyaura cross-coupling strategy

Abstract

In recent years, Pd-catalyzed Suzuki-Miyaura (SM) cross-coupling reactions have revolutionized approaches to carbon-carbon bond formation. We have studied the application of SM coupling with several (ca. 16) complex molecular structures of particular relevance to scientists working at the interfaces of chemistry, biology, and materials sciences. In this regard, various structurally or biologically important polycyclic molecules (e.g., benzocrowns, C₃-symmetric molecules, 9,10-disubstituted anthracenes, and sulfones) and unusual amino acid derivatives have been modified by this reaction, while it has also been shown that allylation of aromatics through the use of a commercially available boronic acid ester by SM coupling under CsF/Pd⁰ conditions is feasible.