Abstract
New well-defined, paramagnetic nickel complexes have been prepared and characterized by X-ray crystallography. The complexes were found to be active for the cross-coupling of alkyl electrophiles (especially ethyl 2-bromobutyrate) with alkyl Grignard reagents. The ligand architecture in these new complexes could potentially be rendered chiral, opening up future possibilities for performing asymmetric cross-coupling reactions.
Highlights
The realization of efficient and transition metal catalyzed alkyl-alkyl cross-coupling reactions poses significant challenges
The aryl amine group could be rendered chiral, for instance as a 2,5-dimethylpyrrolidine ligand, for potential asymmetric reactions [13]. With these considerations in mind, we explored the synthesis of new aminophenolate complexes of nickel in order to test their competency in organic cross-coupling reactions
While dimer 4 was only formed in minor amounts, red orange crystals of 4 could be separated from the yellow/beige 5 under a microscope in order to investigate its structure by X-ray crystallography
Summary
The realization of efficient and transition metal catalyzed alkyl-alkyl cross-coupling reactions poses significant challenges. It must be taken into account that alkyl halides can react with transition metals by one-electron processes affording alkyl radicals, which must be tamed to participate in a selective reaction. Despite these inherent obstacles, much progress has been made in recent years in identifying active catalysts for alkyl-alkyl cross-coupling reactions, especially based on nickel [1,2,3,4,5,6,7]. Much focus is dedicated to developing new catalysts for coupling secondary alkyl electrophiles, with the hope that the coupling reactions could be rendered enantioselective [5,6,8,9,10]
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