<i>trans</i>-Dichlorobis(XPhos)palladium(II) Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl/Vinyl Sulfonates/Halides: Scope, Mechanistic Study, and Synthetic Applications
Fatih Sirindil, Romain Pertschi, Emma Naulin, Delphine Hatey, Jean‐Marc Weibel, Patrick Pale, Aurélien Blanc
Abstract
Suzuki-Miyaura cross-coupling reactions of aryl/vinyl sulfonates/halides with various boron species were performed using an easily available trans-dichlorobis(XPhos)palladium(II) precatalyst. Under microwave assistance, more than 30 coupling products were obtained with yields ranging from 23 to 99%, including the synthesis of two bioactive compounds, dubamine and tamoxifen. A mechanistic investigation of the Suzuki-Miyaura reaction was conducted notably by nuclear magnetic resonance (NMR) and high-resolution mass spectroscopy, revealing the nature of the active Pd 0 species and of the reducing entity.
Topics & Concepts
PalladiumArylHalideChemistryCoupling reactionOrganic chemistryCatalysisCombinatorial chemistryAlkylCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis TechniquesChemical synthesis and alkaloids