Synfacts 2006(7): 0721-0721  
DOI: 10.1055/s-2006-941882
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Suzuki Reaction of Unactivated Alkyl Halides

Contributor(s): Paul Knochel, Andrei Gavryushin
F. González-Bobes, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
Further Information

Publication History

Publication Date:
22 June 2006 (online)

Significance

This is a further significant development in the field of the cross-coupling reaction of alkyl electrophiles. Inexpensive amino alcohols were found to serve as efficient catalysts for the coupling of primary and secondary alkyl chlorides with arylboronic acids. The same catalyst, trans-2-aminocyclohexanol, can be successfully applied for the Suzuki coupling of any primary and secondary alkyl halide. The formation of a radical intermediate during the oxidative addition of nickel has been proved.