Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide

Valerie Schmidt describes an intermolecular anti-Markovnikov hydroamination of alkenes.

Nitrogen atoms are ubiquitous in pharmaceuticals, natural products, materials, and commodity chemicals. The simplest amine – ammonia – is central to life since its use as fertilizer quite literally feeds the world. Biological systems are finely tuned to use ammonia as a building block for complex molecule synthesis, but the use of ammonia in the laboratory is met with many obstacles ranging from the conceptual to the practical which have impeded the usage of ammonia directly in synthetic methodology development. Professor Valerie A. Schmidt from the University of California, San Diego (USA) and her group considered that an inexpensive ammonia surrogate could be used to create new C–N bonds via alkene hydroamination. In an effort to realize this, they investigated N-hydroxyphthalimide (NHPI) as a potential ammonia surrogate.

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