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Synthesis and structural characterization of stable organogold(I) compounds. evidence for the mechanism of gold-catalyzed cyclizations

Journal of the American Chemical Society, ISSN: 0002-7863, Vol: 130, Issue: 52, Page: 17642-17643
2008
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Article Description

The vast majority of homogeneous Au-catalyzed reactions have exploited the propensity of Au to activate unsaturated carbon-carbon bonds as electrophiles. It is generally assumed that a nucleophile attacks a gold-activated carbon-carbon multiple bond to give an alkenyl Au intermediate, notwithstanding the fact that these intermediates are hitherto unknown. We have obtained room temperature stable A-lactone gold(I) complexes through the reaction of cationic Au(I) reagents with allenoates, under mild conditions. The reactions of one such complex with electrophiles yielded the expected products of Au-catalyzed cyclizations. These results furnish experimental evidence for the mechanism of Au-catalyzed cyclizations. Copyright © 2009 American Chemical Society.

Bibliographic Details

Liu, Le-Ping; Xu, Bo; Mashuta, Mark S; Hammond, Gerald B

American Chemical Society (ACS)

Chemical Engineering; Chemistry; Biochemistry, Genetics and Molecular Biology

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