Palladium-catalyzed aerobic oxidative dehydrogenation of cyclohexenes to substituted arene derivatives.
A palladium(II) catalyst system has been identified for aerobic dehydrogenation of substituted cyclohexenes to the corresponding arene derivatives. Use of sodium anthraquinone-2-sulfonate (AMS) as a cocatalyst enhances the product yields. A wide range of functional groups are tolerated in the reactions, and the scope and limitations of the method are described. The catalytic dehydrogenation of cyclohexenes is showcased in an efficient route to a phthalimide-based TRPA1 activity modulator.
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Andrei V
AV
Iosub
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Shannon S
SS
Stahl
D000880:Anthraquinones / Q000737:chemistry; D002384:Catalysis; D053138:Cyclohexenes / Q000737:chemistry* / Q000494:pharmacology; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006865:Hydrogenation; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D050051:Transient Receptor Potential Channels / Q000378:metabolism
D000880:Anthraquinones; D053138:Cyclohexenes; D006841:Hydrocarbons, Aromatic; D050051:Transient Receptor Potential Channels; C023554:anthraquinone sulfonate; D010165:Palladium; D010100:Oxygen