Standard Article

Formation of Carbon-Carbon Bonds via π-Allylnickel Compounds

  1. Martin F. Semmelhack

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or019.02

Organic Reactions

Organic Reactions

How to Cite

Semmelhack, M. F. 2011. Formation of Carbon-Carbon Bonds via π-Allylnickel Compounds. Organic Reactions. 19:2:115–198.

Author Information

  1. Cornell University, Ithaca, New York

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

Choose one or more boxes to highlight terms.


Transition metal complexes containing a planar three-carbon ligand, the pi-allyl group was first described in 1958 with the discovery of (pi-1-methylallyl)cobalt tricarbonyl. After this discovery, many other syntheses followed. This chapter deals with synthetic organic applications of pi-allylnickel complexes. At this time, the study of this subject is in its infancy. The unifying aspect of pi-allylnickel chemistry is the ability of the allyl ligand to form new carbon-carbon bonds.


  • carbon-carbon bonds;
  • pi-allylnickel compounds;
  • discrete reagents;
  • transient intermediates;
  • halides;
  • carbonylation;
  • allylic halides;
  • nickel carbonyl;
  • bis(pi-allyl)nickel complexes;
  • experimental procedures