Suzuki–Miyaura Cross-Coupling of Aryl Fluorosulfonates Mediated by Air- and Moisture-stable [Pd(NHC)(μ-Cl)Cl]<sub>2</sub>Precatalysts: Broad Platform for C–O Cross-Coupling of Stable Phenolic Electrophiles
Shiyi Yang, Hengzhao Li, Xiang Yu, Jie An, Michal Szostak
Abstract
A highly efficient protocol for the Suzuki–Miyaura cross-coupling of aryl fluorosulfonates by selective −OF cleavage using well-defined, air- and moisture-stable NHC-Pd(II) chloro dimers is presented. The reaction proceeds in excellent yields and with broad functional group tolerance using 0.10–0.20 mol % of [Pd] in the presence of mild K3PO4 base under aqueous conditions. A variety of sensitive functional groups are tolerated in this operationally trivial protocol for C–O bond activation. Selectivity studies and gram scale cross-coupling are presented. The method advances well-defined and highly reactive Pd(II)-NHCs to the cross-coupling of readily available, orthogonal, and bench-stable fluorosulfonates as aryl halide surrogates.