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

ABSTRACT: We report a convenient preparation of a new and storable magnesium amide (iPr₂ 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.

SUBMITTER: Hess A

PROVIDER: S-EPMC9401567 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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

Hess Andreas A Alandini Nurtalya N Guersoy Yusuf C YC Knochel Paul P

Angewandte Chemie (International ed. in English) 20220601 29

We report a convenient preparation of a new and storable magnesium amide (iPr2 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 ...[more]

PMID: 35575962

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