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Highly Regioselective Preparation of Heteroaryl–Magnesium Reagents by Using a Br/Mg Exchange
Author(s) -
Sämann Christoph,
Haag Benjamin,
Knochel Paul
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202230
Subject(s) - regioselectivity , negishi coupling , reagent , chemistry , magnesium bromide , magnesium , lithium (medication) , lithium bromide , bromide , medicinal chemistry , chloride , ligand (biochemistry) , organic chemistry , diamine , combinatorial chemistry , catalysis , biochemistry , physics , receptor , heat exchanger , thermodynamics , endocrinology , medicine
Disubstituted thienyl‐, furyl‐ and pyridylmagnesium derivatives are regioselectively prepared from a Br/Mg exchange of the corresponding dibromo compounds by using either i PrMgCl ⋅ LiCl or hindered arylmagnesium reagents, such as isitylmagnesium bromide ⋅ lithium chloride (isityl=2,4,6‐triisopropyl‐phenyl) complexed with a diamine ligand, in difficult cases. The selective functionalisations of these heterocyclic scaffolds by using Negishi cross‐coupling reactions, acylations or addition to aldehydes were readily achieved.