Journal
SCIENCE
Volume 364, Issue 6442, Pages 764-+Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aaw3913
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Funding
- National Science Foundation [CHE-1401049]
- Deutsche Forschungsgemeinschaft [Ga 619/11-1, Ga 619/12-1]
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The opening of epoxides typically requires electrophilic activation, and subsequent nucleophilic (S(N)2) attack on the less substituted carbon leads to alcohols with Markovnikov regioselectivity. We describe a cooperative catalysis approach to anti-Markovnikov alcohols by combining titanocene-catalyzed epoxide opening with chromium-catalyzed hydrogen activation and radical reduction. The titanocene enforces the anti-Markovnikov regioselectivity by forming the more highly substituted radical. The chromium catalyst sequentially transfers a hydrogen atom, proton, and electron from molecular hydrogen, avoiding a hydride transfer to the undesired site and resulting in 100% atom economy. Each step of the interconnected catalytic cycles was confirmed separately.
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