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The article that inspired this work describes a new method for directly adding nitrogen-containing groups and halogens (chlorine or bromine) to alkenes (carbon-carbon double bonds) in a single step. The key reagents used are multifunctional hydroxylamines (MFHAs), which can simultaneously introduce a nitrogen-containing group and a halogen onto the alkene. This approach allows for the rapid synthesis of structurally complex amines and nitrogen-containing heterocycles, which are important scaffolds in pharmaceuticals and other bioactive molecules.
The researchers optimized the reaction conditions and explored the scope of alkene substrates, including styrenes, aliphatic cyclic and linear alkenes, and even enynes. They demonstrated that both electron-rich and electron-deficient alkenes can undergo this difunctionalization reaction, providing a diverse range of MFHA products in good to excellent yields.
Furthermore, the authors showcased the synthetic utility of the MFHA products by performing various complexity-building transformations. These include aziridine formation, nucleophilic substitution of the halogen, transition metal-catalyzed cross-coupling reactions, and intramolecular rearrangements, highlighting the versatility of MFHAs as synthetic building blocks for structurally complex amines and heterocycles