TCI Pick : Anti-Markovnikov Hydration of Vinylarenes via Triple Relay Catalysis
Grubbs et al. have reported a direct and selective synthesis of primary alcohols (anti-Markovnikov hydration) from nonactivated vinylarenes using a triple relay catalysis system. They have proposed that the catalytic system couples palladium-catalyzed oxidation of vinylarenes to tert-butyl vinyl ethers, acid-catalyzed hydrolysis of the vinyl ethers to aldehydes, and ruthenium (Shvo’s catalyst)-catalyzed transfer hydrogenation of the aldehydes to primary alcohols.
G. Dong, P. Teo, Z. K. Wickens, R. H. Grubbs, Science 2011, 333, 1609.
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