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

作者: G. Dong , P. Teo , Z. K. Wickens , R. H. Grubbs

DOI: 10.1126/SCIENCE.1208685

关键词: Olefin fiberBoranePrimary (chemistry)ChemistryRegioselectivityOrganic chemistryMarkovnikov's ruleYield (chemistry)CatalysisHydroboration

摘要: Alcohol synthesis is critical to the chemical and pharmaceutical industries. The addition of water across olefins 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 oxidant currently most practical methodology. Here, we report more direct approach with use triple relay catalysis system that couples palladium-catalyzed oxidation, acid-catalyzed hydrolysis, ruthenium-catalyzed reduction cycles. Aryl-substituted terminal are converted by net in good yield excellent regioselectivity.

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