Sulfur(vi) fluoride exchange and modular diazotransfer reactions have advanced click chemistry, but their mechanisms and reactivity profiles are not well understood. Now, a computational study of these reactions provides mechanistic insights and predictive reactivity models for modular diazotransfer, facilitating the development of an easy-to-prepare and -handle diazotransfer reagent with excellent reactivity.
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References
Kolb, H. C., Finn, M. G. & Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004–2021 (2001). A review article that presents the concept of click chemistry.
Dong, J., Krasnova, L., Finn, M. G. & Sharpless, K. B. Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry. Angew. Chem. Int. Ed. 53, 9430–9448 (2014). A review article that presents the concept of SuFEx chemistry.
Meng, G. et al. Modular click chemistry libraries for functional screens using a diazotizing reagent. Nature 574, 86–89 (2019). This paper reports the discovery of a robust diazotransfer reagent, fluorosulfuryl azide, that has facilitated the development of the modular diazotransfer reaction.
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This is a summary of: Zheng, M.-M. et al. Computational analysis of modular diazotransfer reactions for the development of predictive reactivity models and diazotransfer reagents. Nat. Synth. https://doi.org/10.1038/s44160-024-00633-2 (2024).
M.-M.Z. and X.-S.X. used WeTab AI Pro to help prepare their contribution to this Research Briefing.
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Computationally guided design of a diazotransfer reagent with high reactivity. Nat. Synth (2024). https://doi.org/10.1038/s44160-024-00634-1
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DOI: https://doi.org/10.1038/s44160-024-00634-1
