Solvent Effects on the Selectivity of Palladium-Catalyzed Suzuki-Miyaura Couplings.

ABSTRACT: The use of polar solvents MeCN or dimethylformamide (DMF) was previously shown to induce a selectivity switch in the Pd/P ^t Bu₃-catalyzed Suzuki-Miyaura coupling of chloroaryl triflates. This phenomenon was attributed to the ability of polar solvents to stabilize anionic transition states for oxidative addition. However, we demonstrate that selectivity in this reaction does not trend with solvent dielectic constant. Unlike MeCN and DMF, water, alcohols, and several polar aprotic solvents such as MeNO₂, acetone, and propylene carbonate provide the same selectivity as nonpolar solvents. These results indicate that the role of solvent on the selectivity of Suzuki-Miyaura couplings may be more complex than previously envisioned. Furthermore, this observa

SUBMITTER: Reeves EK 

PROVIDER: S-EPMC7566783 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature