Dinitrogen extrusion from diazene in organic synthesis |
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Institution: | 1. Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China;2. National Engineering Research Center of Chemical Fertilizer Catalyst, College of Chemical Engineering, Fuzhou University, Fuzhou 350108, China;3. Max Planck Institute of Molecular Physiology, Department of Chemical Biology, Dortmund 44227, Germany |
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Abstract: | Radical-mediated reactions have many advantages in the construction of complex molecular scaffolds by forging chemical bonds of high challenge. Diazenes, including 1,1-diazenes and 1,2-diazenes, can generate biradical species via nitrogen extrusion under thermal or photochemical conditions. The superior reactivity of the generated biradical enables various types of synthetic transformations with excellent chemoselectivity and has been applied to the complex natural products synthesis. In this mini-review, the modes of reaction are summarized and discussed, namely ring contraction via nitrogen deletion, homo or hetero-dimerization, trimethylenemethane (TMM)-diyl cycloaddition. Applications of these classes of reactions in complex natural product synthesis are illustrated. Last but not least, the current state, future directions, and opportunities for dinitrogen extrusion reaction from diazenes are highlighted and discussed. |
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