Primary Alcohols from Terminal Olefins: Formal Anti-Markovnikov Hydration via Triple Relay Catalysis
Online Publication Date2011-09-15
Print Publication Date2011-09-16
Permanent link to this recordhttp://hdl.handle.net/10754/599400
MetadataShow full item record
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.
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.
SponsorsWe 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.
CollectionsPublications Acknowledging KAUST Support
- New reactions of 1-alkynes catalyzed by transition metal complexes.
- Authors: Wakatsuki Y, Hou Z, Tokunaga M
- Issue date: 2003
- Direct Anti-Markovnikov Addition of Water to Olefin To Synthesize Primary Alcohols: A Theoretical Study.
- Authors: Ceylan YS, Cundari TR
- Issue date: 2019 Jan 31
- Anti-Markovnikov oxidation and hydration of terminal olefins.
- Authors: Guo J, Teo P
- Issue date: 2014 May 21
- A general and efficient catalyst for palladium-catalyzed C-O coupling reactions of aryl halides with primary alcohols.
- Authors: Gowrisankar S, Sergeev AG, Anbarasan P, Spannenberg A, Neumann H, Beller M
- Issue date: 2010 Aug 25
- Palladium-catalyzed Markovnikov terminal arylalkynes hydrostannation: application to the synthesis of 1,1-diarylethylenes.
- Authors: Hamze A, Veau D, Provot O, Brion JD, Alami M
- Issue date: 2009 Feb 6