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![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Photoredox/Cobalt-Catalyzed Cascade Rearrangement-Cyclization of Alkene
Kanaru Sasaki1, Bartłomiej Szarłan2, Takashi Fujihara3
1Faculty of Pharmacy, Musashino University, 1-1-20 Shinmachi, Nishitokyo, Tokyo202-8585, Japan.
Abstract:
A photoredox/cobalt-catalyzed sequential rearrangement-cyclization of unactivated alkenes is reported. 1,1-Diarylalkenes bearing tethered nucleophiles undergo a selective 1,2-aryl migration, initiated by metal-hydride hydrogen atom transfer and radical-polar crossover, followed by intramolecular cyclization. Evaluating the catalytic reaction manifolds suggested that this system offers high reactivity and migratory selectivity. The preference for the 1,2-aryl shift over direct cyclization was rationalized by DFT calculations. This catalytic protocol enables accessing diverse spirocyclic and heterocyclic architectures.
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