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Published September 16, 2011 | Supplemental Material
Journal Article Open

Primary Alcohols from Terminal Olefins: Formal Anti-Markovnikov Hydration via Triple Relay Catalysis


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.

Additional Information

© 2011 American Association for the Advancement of Science. Received 20 May 2011; accepted 27 July 2011. We gratefully acknowledge financial support from the King Abdullah University of Science and Technology Center in Development, King Fahd University of Petroleum and Minerals, and the NSF. G.D. thanks the Camille and Henry Dreyfus Foundation for a postdoctoral fellowship. P.T. thanks A*STAR (Agency for Science, Technology and Research) for a postdoctoral fellowship (2009 to 2011). P.T. and Z.K.W. contributed equally to this paper. We also thank V. Lavallo and B. K. Keitz for proofreading the manuscript. A provisional patent was filed for work described in this Report.

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