Synfacts 2010(7): 0820-0820  
DOI: 10.1055/s-0029-1220046
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Iron-Catalyzed C-C Bond Formation via 1,5-Hydrogen Transfer

Contributor(s): Paul Knochel, Tobias Thaler
N. Yoshikai, A. Mieczkowski, A. Matsumoto, L. Ilies, E. Nakamura*
The University of Tokyo, Japan
Further Information

Publication History

Publication Date:
22 June 2010 (online)

Significance

An iron-catalyzed C-C coupling at the α-position of aliphatic amines via C-H bond activation through 1,5-hydrogen transfer was discovered. The reaction is proposed to proceed via radical formation at the 2-iodobenzyl group promoted by the organoiron reagent. This is followed by a 1,5-hydrogen transfer. The C(sp³)-C(sp²) bond formation is thought to take place via an ­organoiron intermediate.