A robustness screen for the rapid assessment of chemical reactions

Abstract

In contrast to the rapidity with which scientific information is published, the application of new knowledge often remains slow, and we believe this to be particularly true of newly developed synthetic organic chemistry methodology. Consequently, methods to assess and identify robust chemical reactions are desirable, and would directly facilitate the application of newly reported synthetic methodology to complex synthetic problems. Here, we describe a simple process for assessing the likely scope and limitations of a chemical reaction beyond the idealized reaction conditions initially reported. Using simple methods and common analytical techniques we demonstrate a rapid assessment of an established chemical reaction, and also propose a simplified analysis that may be reported alongside new synthetic methodology.

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Figure 1: A typical palladium-catalysed Suzuki–Miyaura cross-coupling.
Figure 2: Results of the preparation of multifunctional substrates to validate the predictions of the robustness screen.

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Acknowledgements

Dedicated to Prof. R. W. Hoffmann on the occasion of his 80th birthday. The authors acknowledge financial support from the European Research Council under the European Community's Seventh Framework Program (FP7 2007–2013)/ERC Grant agreement (no. 25936) and the Deutsche Forschungsgemeinschaft (DFG, Leibniz award to F.G.). The authors thank C. Richter and D. Tang for helpful discussions.

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F.G. and K.D.C. conceived the concept and experiments. K.D.C. performed all experiments. Both authors discussed the results and co-wrote the paper.

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Correspondence to Frank Glorius.

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The authors declare no competing financial interests.

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Collins, K., Glorius, F. A robustness screen for the rapid assessment of chemical reactions. Nature Chem 5, 597–601 (2013). https://doi.org/10.1038/nchem.1669

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