Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides

The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl 2 and ( R , R )-QuinoxP*, lithium arylborates are cross-coupled with tert -butyl α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. ( R , R )-QuinoxP* is specifically able to induce chirality when compared to analogous P -chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system. The first iron-catalyzed enantioselective Suzuki-Miyaura coupling reaction has been established by using electron-deficient P -chiral bisphosphine ligand ( R , R )-QuinoxP*.