A general and efficient catalyst system for a Wacker-type oxidation using TBHP as the terminal oxidant: application to classically challenging substrates.
Utilizing the rapidly synthesized Quinox ligand and commercially available aqueous TBHP, a Wacker-type oxidation has been developed, which efficiently converts the traditionally challenging substrate class of protected allylic alcohols to the corresponding acyloin products. Additionally, the catalytic system is general for several other substrate classes, converting terminal olefins to methyl ketones, with short reaction times. The system is scalable (20 mmol) and can be performed with a reduced catalyst loading of 1 mol%. Enantioenriched substrates undergo oxidation with complete retention of enantiomeric excess.
Michel
Brian W
BW
Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah 84112-085, USA.
Camelio
Andrew M
AM
Cornell
Candace N
CN
Sigman
Matthew S
MS
D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D020122:tert-Butylhydroperoxide / Q000737:chemistry*
D000475:Alkenes; D007659:Ketones; D010165:Palladium; D020122:tert-Butylhydroperoxide