Regioselective Magnesiations of Fluorinated Arenes and Heteroarenes Using Magnesium-bis-Diisopropylamide (MBDA) in Hydrocarbons

Hess, Andreas; Alandini, Nurtalya; Guersoy, Yusuf C. and Knochel, Paul (2022): Regioselective Magnesiations of Fluorinated Arenes and Heteroarenes Using Magnesium-bis-Diisopropylamide (MBDA) in Hydrocarbons. In: Angewandte Chemie International Edition, Vol. 61, No. 29

Abstract

We report a convenient preparation of a new and storable magnesium amide (iPr(2)N)(2)Mg (magnesiumbis-diisopropylamide;MBDA) which proved to be especially suitable for the non-cryogenic magnesiation of fluoro-substituted arenes and heteroarenes providing arylmagnesium amides (ArMgDA) or bis-heteroaryl magnesiums (HetAr)(2)Mg in hydrocarbons. Further reactions with electrophiles (aldehydes, ketones, allylic bromides, aryl halides (Negishi cross-coupling)) furnished a range of polyfunctional fluoro-substituted unsaturated building blocks. Several postfunctionalizations were described as well as NMR-studies confirming the dimeric structure of the base.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1433-7851
• Language: English
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 491502892