Mechanism of the palladium-catalyzed intramolecular hydroalkylation of 7-octene-2, 4-dione

H Qian, RA Widenhoefer

Index: Qian, Hua; Widenhoefer, Ross A. Journal of the American Chemical Society, 2003 , vol. 125, # 8 p. 2056 - 2057

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Citation Number: 84

Abstract

Cyclization of (E)-7, 8-dideuterio-7-octene-2, 4-dione [(E)-1-7, 8-d 2] catalyzed by PdCl2 (CH3CN) 2 (2) formed cis-2-acyl-3, 4-dideuteriocyclohexanone (cis-3-3, 4-d 2) in 64% yield as the exclusive isotopomer. This experiment, in conjunction with additional deuterium labeling experiments, was in accord with a mechanism for the conversion of 1 to 3 catalyzed by 2 involving attack of the enol carbon atom on a palladium-complexed olefin followed by ...