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

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

Research output: Contribution to journalArticlepeer-review

135 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)1609-1612
Number of pages4
JournalScience
Volume333
Issue number6049
DOIs
StatePublished - Sep 15 2011
Externally publishedYes

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