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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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
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author Hess, Andreas
Alandini, Nurtalya
Guersoy, Yusuf C.
Knochel, Paul
author_facet Hess, Andreas
Alandini, Nurtalya
Guersoy, Yusuf C.
Knochel, Paul
author_sort Hess, Andreas
collection PubMed
description 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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spelling pubmed-94015672022-08-26 Regioselective Magnesiations of Fluorinated Arenes and Heteroarenes Using Magnesium‐bis‐Diisopropylamide (MBDA) in Hydrocarbons Hess, Andreas Alandini, Nurtalya Guersoy, Yusuf C. Knochel, Paul Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2022-06-01 2022-07-18 /pmc/articles/PMC9401567/ /pubmed/35575962 http://dx.doi.org/10.1002/anie.202206176 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Hess, Andreas
Alandini, Nurtalya
Guersoy, Yusuf C.
Knochel, Paul
Regioselective Magnesiations of Fluorinated Arenes and Heteroarenes Using Magnesium‐bis‐Diisopropylamide (MBDA) in Hydrocarbons
title Regioselective Magnesiations of Fluorinated Arenes and Heteroarenes Using Magnesium‐bis‐Diisopropylamide (MBDA) in Hydrocarbons
title_full Regioselective Magnesiations of Fluorinated Arenes and Heteroarenes Using Magnesium‐bis‐Diisopropylamide (MBDA) in Hydrocarbons
title_fullStr Regioselective Magnesiations of Fluorinated Arenes and Heteroarenes Using Magnesium‐bis‐Diisopropylamide (MBDA) in Hydrocarbons
title_full_unstemmed Regioselective Magnesiations of Fluorinated Arenes and Heteroarenes Using Magnesium‐bis‐Diisopropylamide (MBDA) in Hydrocarbons
title_short Regioselective Magnesiations of Fluorinated Arenes and Heteroarenes Using Magnesium‐bis‐Diisopropylamide (MBDA) in Hydrocarbons
title_sort regioselective magnesiations of fluorinated arenes and heteroarenes using magnesium‐bis‐diisopropylamide (mbda) in hydrocarbons
topic Communications
url 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
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