Palladium(II)-catalyzed aerobic hydroalkoxylation of styrenes containing a phenol.
An intermolecular Pd-catalyzed hydroalkoxylation of styrenes that contain a phenol is presented. The reaction can be performed on terminal, disubstituted, and trisubstituted olefins in a variety of alcoholic solvents. Initial mechanistic data suggest a mechanism that involves oxidation of the alcoholic solvent to provide a Pd-hydride that inserts into an olefin. This is followed by formation of a quinone methide and subsequent addition of an alcohol to yield the hydroalkoxylated product.
Gligorich
Keith M
KM
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112-0850, USA.
Schultz
Mitchell J
MJ
Sigman
Matthew S
MS
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis*; D006900:Hydroxylation; D045563:Indolequinones / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry*
D000475:Alkenes; D004987:Ethers; D045563:Indolequinones; D007659:Ketones; D010636:Phenols; D013343:Styrenes; C068040:quinone methide; D010165:Palladium