Science of Synthesis

Scholz, U.; Schlummer, B., Science of Synthesis, (2007) 31, 1617.

Arylmagnesium halides are simply converted into the corresponding arylzincates, which themselves may serve as starting materials for a replacement of zinc with amines with the help of a nickel–phosphine catalyst. However, only benzoyloxy-protected amines can be used as the amine reagent, yields are rather low, and the reaction conditions have not yet been developed into a practical procedure. As an example, (4-cyanophenyl)magnesium chloride and 4-(benzoyloxy)morpholine form 4-morpholinobenzonitrile (‌130‌) in an acceptable yield (‌Scheme 139‌).[‌225‌]

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References