C-C Bond Activation

19 November, 2015 / by SK / in Reactions

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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

<reviews>
・Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610. DOI: 10.1039/B308864M
・Kondo, T.; Mitsudo, T. Chem. Lett. 2005, 11, 1462. doi:10.1246/cl.2005.1462
・Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 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 2014, 512, 413. DOI:10.1038/nature13624
[3] Nakao, Y. Bull. Chem. Soc. Jpn. 2012, 85, 731. doi:10.1246/bcsj.20120081