Pd-Catalyzed O-Arylation of Phenols Mediated by a Weak, Soluble Organic Base: Methodology, Mechanism, and Compatibility with Enabling Technologies

prediction of reaction outcome as a function of substrate electronics, and provides an intuitive guide as to how diaryl ether targets should be disconnected. The resulting methodology exhibits broad substrate scope, with yields reproducible across both preparative 'singleton' scales and high throughput formats. The homogeneous nature of the couplings allows their safe execution under microwave heating, with elevated temperatures allowing for short reaction times even in the presence of air, and their facile translation to scale-up in continuous flow.