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E-Olefins through intramolecular radical relocation
, Theresa Sperger, Sinem Guven, Franziska Schoenebeck
Published in
Volume: 363
Issue: 6425
Pages: 391 - 396
Full control over the selectivity of carbon-carbon double-bond migrations would enable access to stereochemically defined olefins that are central to the pharmaceutical, food, fragrance, materials and petrochemical arenas. The vast majority of double-bond migrations investigated over the past 60 years capitalize on precious-metal hydrides that are frequently associated with reversible equilibria, hydrogen scrambling, incomplete E/Z stereoselection and/or high cost. Here, we report a fundamentally different, radical-based approach.We showcase a nonprecious, reductant-free and atom-economical nickel (Ni)(I)-catalyzed intramolecular 1,3-hydrogen atom relocation to yield E-olefins within 3 hours at room temperature. Remote installations of E-olefins over extended distances are also demonstrated.
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