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  • Title: Primary alcohols from terminal olefins: formal anti-Markovnikov hydration via triple relay catalysis.
    Author: Dong G, Teo P, Wickens ZK, Grubbs RH.
    Journal: Science; 2011 Sep 16; 333(6049):1609-12. PubMed ID: 21921194.
    Abstract:
    Alcohol synthesis is critical to the chemical and pharmaceutical industries. The addition of water across olefins to form primary alcohols (anti-Markovnikov olefin hydration) would be a broadly useful reaction but has largely proven elusive; an indirect hydroboration/oxidation sequence requiring stoichiometric borane and oxidant is currently the most practical methodology. Here, we report a more direct approach with the use of a triple relay catalysis system that couples palladium-catalyzed oxidation, acid-catalyzed hydrolysis, and ruthenium-catalyzed reduction cycles. Aryl-substituted terminal olefins are converted to primary alcohols by net reaction with water in good yield and excellent regioselectivity.
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