The generation of nucleophiles from the combination of aryl boronic acids and catalytic amounts of copper salt allows a reactivity distinct from other organometallic species, such as organolithiums or Grignard reagents. Here we examine how the electronic and steric properties of the boronic acid affect the formation of active nucleophiles and their subsequent reactivity with iminium-type compounds, showing that electron-rich substrates display reduced reactivity.

Das Perfluormethylpenten (I) reagiert mit den Grignard‐Reagenzien (II) bzw. (V) unter 7‐ und α‐Fluoreliminierung zu den substituierten Alkenen (III) und (IV) bzw. (VI) und (VII).