C-C Bond Activation

C-C Bond Activation

  • General Characteristics

Carbon-carbon bonds are among the strongest in organic compounds. Activating them for useful chemical transformation is one of the newest and biggest challenges in organic synthesis. Efficient C-C bond activation would contribute not only to atom economy but also to the development of novel synthetic strategies and the discovery of unknown compounds.

Although olefin metathesis is regarded as a successful example, the cleavage of C-C single bonds lacks “handles” and remains as a major challenge. Limited cases involving transition metal catalysis rely on coordinating groups and ring strain of the substrates.

  • General References

・Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610. DOI: 10.1039/B308864M
・Kondo, T.; Mitsudo, T. Chem. Lett. 200511, 1462. doi:10.1246/cl.2005.1462
・Murakami, M.; Matsuda, T. Chem. Commun. 201147, 1100. DOI: 10.1039/C0CC02566F
・Nakao, Y. Bull. Chem. Soc. Jpn. 2012, 85, 731. doi:10.1246/bcsj.20120081

  • Reaction Mechanism

  • Examples

The total synthesis of cycloinumakiol based on the C-C bond activation as a key step.[1]


The cleavage of benzene ring.[2]


The carbocyanation of alkynes by Ni catalysis.[3]


  • Experimental Procedure

  • Experimental Tips

  • References

[1] Xu, T.; Dong, G. Angew. Chem. Int. Ed. 2014, 53,10773. DOI: 10.1002/anie.201404802
[2] Hu, S.; Shima, T.; Hou, Z. Nature 2014512, 413. DOI:10.1038/nature13624
[3] Nakao, Y. Bull. Chem. Soc. Jpn. 2012, 85, 731. doi:10.1246/bcsj.20120081

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  • External Links