Silver-Catalysed Hydroarylation of Highly Substituted Styrenes

Dalton, Toryn; Gressies, Steffen; Das, Mowpriya; Niehues, Maximilian; Schrader, Malte L.; Gutheil, Christian; Ravoo, Bart Jan; Glorius, Frank

Abstract

Hydroarylation is an effective strategy to rapidly increase the complexity of organic structures by transforming flat alkene moieties into three-dimensional frameworks. Many strategies have already been developed to achieve the hydroarylation of styrenes, however most of these reports examine the hydroarylation of unpolar, β-mono- or β-unsubstituted styrenes, while exploring mainly electron-rich benzene nucleophiles. Herein, we report a mild and general catalytic system for the selective hydroheteroarylation of multiply substituted styrenes and heteroaromatic styrenes. Mechanistic analysis of the reaction led to the discovery of commercially available 2,2′:5′,2′′-terthiophene as a key reagent.