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.