Towards Iron-Catalysed Suzuki Biaryl Cross-Coupling: Unusual Reactivity of 2-Halobenzyl Halides

Abstract

The reaction of 2-halobenzyl halides with the borate anion Li[(Ph)(t-Bu)Bpin] leads not only to the expected arylation at the benzyl position, but also to some Suzuki biaryl cross-coupling. Preliminary mechanistic investigations hint towards the intermediacy of benzyl iron intermediates that can either: (a) directly cross-couple with the aryl boron reagent to give observed monoarylated species, or (b) undergo oxidative addition of the aryl halide to generate the diarylated species on reaction with the boron-based nucleophile.

Key words

iron - cross-coupling - aryl - Suzuki reaction - organoborate

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