title: Primary alcohols from terminal olefins: formal anti-Markovnikov hydration via triple relay catalysis.
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.
authors.affiliation: Arnold and Mabel Beckman Laboratories for Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
authors.forename: Guangbin
authors.initials: G
authors.lastname: Dong
authors.forename: Peili
authors.initials: P
authors.lastname: Teo
authors.forename: Zachary K
authors.initials: ZK
authors.lastname: Wickens
authors.forename: Robert H
authors.initials: RH
authors.lastname: Grubbs