The modern Ullmann coupling (aka Ullmann ether synthesis, Ullmann-type reaction) is a copper or palladium catalyzed C-O bond forming reaction that is most often used for the synthesis of diaryl ethers in natural products or pharmaceuticals. Normally, an inorganic base is used for deprotonation of a phenol to form an anionic phenoxide necessary for the coupling reaction. However, the emergence of catalytic desilylation methodologies suggests that a phenoxide anion can be generated under base-free conditions. Therefore, we hypothesized that desilylation of a silyl ether would reveal a nucleophilic phenoxide species that can be used in Ullmann coupling reactions. We assessed the scope of the reaction by exploring electron-rich, electron-poor, sterically-hindered, and heteroaromatic substrates.

Desilylative Ullmann reaction

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.