Derailing the Wacker oxidation: development of a palladium-catalyzed amidation reaction.
[figure: see text] A conceptually new palladium-catalyzed amidation reaction is described for the synthesis of beta-amido ketones based on derailing the Wacker oxidation of enones. This reaction generates a new carbon-nitrogen bond via a palladium-catalyzed conjugate addition of a carbamate nucleophile to an enone. The regiocontrol, mild and neutral conditions, lack of preactivation of the nucleophile, and lack of reoxidation system for the catalyst are attractive features of this transformation.
Gaunt
M J
MJ
University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K.
Spencer
J B
JB
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D000664:Amphibian Venoms / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000577:Amides; D000596:Amino Acids; D000664:Amphibian Venoms; D002219:Carbamates; D007659:Ketones; C004792:perhydrohistrionicotoxin; D010165:Palladium