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

We report a convenient preparation of a new and storable magnesium amide (iPr(2)N)(2)Mg (magnesium‐bis‐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‐hetero...

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Detalles Bibliográficos
Autores principales: Hess, Andreas, Alandini, Nurtalya, Guersoy, Yusuf C., Knochel, Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401567/
https://www.ncbi.nlm.nih.gov/pubmed/35575962
http://dx.doi.org/10.1002/anie.202206176
Descripción
Sumario:We report a convenient preparation of a new and storable magnesium amide (iPr(2)N)(2)Mg (magnesium‐bis‐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.

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