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Iron-Catalyzed C[BOND]C Bond Formation with C[BOND]H Bond Activation

Organoiron Compounds (2013)

  1. Naohiko Yoshikai

Published Online: 22 OCT 2012

DOI: 10.1002/9780470682531.pat0655

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Yoshikai, N. 2012. Iron-Catalyzed C[BOND]C Bond Formation with C[BOND]H Bond Activation. Patai's Chemistry of Functional Groups. 3.

Author Information

  1. Nanyang Technological University, Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Singapore 637371, Singapore

Publication History

  1. Published Online: 22 OCT 2012

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Abstract

The past decade has witnessed a significant progress in iron-catalyzed organic transformations including functionalization of otherwise unreactive C[BOND]H bonds. This chapter provides a review on iron-catalyzed C[BOND]C bond forming reactions via C[BOND]H bond functionalization. First, a series of stoichiometric, inner-sphere C[BOND]H bond activation reactions by well-defined iron complexes are summarized, which would serve as the basis for the design of catalytic C[BOND]H functionalizations. Second, iron-catalyzed C[BOND]C bond-forming reactions via C(sp2)[BOND]H bond cleavage are discussed with a particular focus on biaryl-forming reactions via aromatic C[BOND]H bond functionalization. Third, iron-catalyzed C[BOND]C bond-forming reactions via C(sp3)[BOND]H bond cleavage are described. Oxidative coupling reactions between two C[BOND]H fragments, so-called cross-dehydrogenative coupling reactions, are mainly discussed.

Keywords:

  • iron;
  • C[BOND]H bond activation;
  • C[BOND]C bond formation;
  • cross-coupling;
  • organometallic reagents;
  • oxidation;
  • radical reaction