Broad Scope Hydrofunctionalization of Styrene Derivatives Using Iron-Catalyzed Hydromagnesiation

Abstract

The highly regioselective iron-catalyzed formal hydrofunctionalization of styrene derivatives with a diverse range of electrophiles has been developed using a single, operationally simple hydromagnesiation procedure and only commercially available, bench-stable reagents. Using just 0.5 mol % FeCl2·4H2O and N,N,N′,N′-tetramethylethylenediamine, hydromagnesiation and electrophilic trapping have been used to form new carbon–carbon bonds (13 examples) and carbon–heteroatom bonds (5 examples) including the products of formal cross-coupling reactions, hydroboration, hydroamination, hydrosilylation, and hydrofluorination.