Synthesis of aromatic ketones by a transition metal-catalyzed tandem sequence.
Both simple Ag(I) and Au(I) are effective catalysts for a tandem [3,3]-sigmatropic rearrangement/formal Myers-Saito cyclization of propargyl esters to form aromatic ketones. A mechanism in which the metal catalyzes both of these processes through alkyne activation is proposed. By using this method a wide range of aromatic structures including naphthyl, anthracenyl and indole ketones are available from readily available propargyl esters.
Zhao
Jing
J
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Hughes
Colin O
CO
Toste
F Dean
FD
D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D028561:Transition Elements / Q000737:chemistry*
D006841:Hydrocarbons, Aromatic; D007659:Ketones; D028561:Transition Elements; C477257:naphthyl phenyl ketone