Synthesis 2015; 47(12): 1761-1765
DOI: 10.1055/s-0034-1380135
paper
© Georg Thieme Verlag Stuttgart · New York

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

Robin B. Bedford*
School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK   Email: r.bedford@bristol.ac.uk
,
Timothy Gallagher
School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK   Email: r.bedford@bristol.ac.uk
,
Dominic R. Pye
School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK   Email: r.bedford@bristol.ac.uk
,
William Savage
School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK   Email: r.bedford@bristol.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 08 December 2014

Accepted: 07 January 2015

Publication Date:
12 February 2015 (eFirst)

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.

 
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