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Organometallic chemistry

A shortcut to molecular complexity

Nature Chemistry volume 9, pages 298–299 (2017)Cite this article

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A unique transformation for the site-selective cleavage of one C–C single bond and two C–H bonds in sequence has now been developed. This enables a simple carbon skeleton to be reorganized into a significantly more complex form with remarkable efficiency.

The most ubiquitous bonds in organic molecules are σ-bonds such as carbon–carbon (C–C) and carbon–hydrogen (C–H) single bonds, which are electronically nonpolar. C–C σ-bonds are the main constituents of the frameworks of organic molecules, with many C–H bonds on the periphery. Both C–C and C–H bonds are generally robust and it is difficult to selectively cleave a specific bond amongst the many typically found in complex molecules. Historically, the challenge of persuading such nonpolar σ-bonds to participate in synthetic transformations1,2,3,4 attracted limited attention from organic chemists. The transformations of unactivated σ-bonds found in textbooks in organic chemistry are non-specific radical halogenations, cationic rearrangement reactions, Friedel–Crafts reactions and pericyclic reactions. However, site-selective cleavage of these nonpolar σ-bonds can be exploited for the reorganization of organic skeletons. Such approaches have the potential to provide innovative routes to difficult synthetic targets, thus the development of such reactions has been the subject of intense research.

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Figure 1: Catalytic cycle proposed by Lautens and co-workers.

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Authors and Affiliations

  1. Masahiro Murakami and Naoki Ishida are in the Department of Synthetic Chemistry and Biological Chemistry at Kyoto University, Katsura, Kyoto 615-8510, Japan,

    Masahiro Murakami & Naoki Ishida

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  1. Masahiro Murakami
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  2. Naoki Ishida
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Correspondence to Masahiro Murakami.

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Murakami, M., Ishida, N. A shortcut to molecular complexity. Nature Chem 9, 298–299 (2017). https://doi.org/10.1038/nchem.2750

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