Preparation of Polyfunctionalized Grignard Reagents and their Application in Aryne Chemistry

The preparation of polyfunctinalized arynes has been achieved by
the controlled elimination of readily generated 2-magnesiated aryl
arylsulfonates obtained by a low temperature halogen/Mg-exchange
starting from the corresponding iodides. New types of Grignard
reagents via the addition of magnesium aryl thiolates, amides and
selenides to arynes and heteroarynes have been prepared. An easy
access to highly functionalized arylmagnesium reagents prepared by
direct magnesiation of carbocyclic aromatic rings with TMPMgClLiCl
was developed.