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dc.contributor.authorDong, G.
dc.contributor.authorTeo, P.
dc.contributor.authorWickens, Z. K.
dc.contributor.authorGrubbs, R. H.
dc.date.accessioned2016-02-28T05:50:25Z
dc.date.available2016-02-28T05:50:25Z
dc.date.issued2011-09-15
dc.identifier.citationDong G, Teo P, Wickens ZK, Grubbs RH (2011) Primary Alcohols from Terminal Olefins: Formal Anti-Markovnikov Hydration via Triple Relay Catalysis. Science 333: 1609–1612. Available: http://dx.doi.org/10.1126/science.1208685.
dc.identifier.issn0036-8075
dc.identifier.issn1095-9203
dc.identifier.pmid21921194
dc.identifier.doi10.1126/science.1208685
dc.identifier.urihttp://hdl.handle.net/10754/599400
dc.description.abstractAlcohol 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.
dc.description.sponsorshipWe 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.
dc.publisherAmerican Association for the Advancement of Science (AAAS)
dc.titlePrimary Alcohols from Terminal Olefins: Formal Anti-Markovnikov Hydration via Triple Relay Catalysis
dc.typeArticle
dc.identifier.journalScience
dc.contributor.institutionCalifornia Institute of Technology, Pasadena, United States
dc.contributor.institutionKing Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia
dc.contributor.institutionInstitute of Chemical and Engineering Sciences, Singapore City, Singapore
dc.date.published-online2011-09-15
dc.date.published-print2011-09-16


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