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Dehydrogenative Meyer–Schuster-Like Rearrangement: A Gold-Catalyzed Reaction Generating an Alkyne

Authors


  • Y. Yu and W. Yang are grateful to the CSC (Chinese Scholarship Council) for fellowships and they contributed equally to this work. Gold salts were generously provided by Umicore AG & Co. KG.

Abstract

Easily accessible propargylic esters are converted to the inverted alkynyl ketones in an oxidative gold-catalyzed reaction. Gagosz’s catalyst in combination with PhI(OAc)2 is the best system for this conversion and 18 examples with yields up to 80 % are reported. The results indicate that the triple bond in the product is formed by elimination from a vinylgold intermediate. In a formal sense the new conversion overall is a dehydrogenative Meyer–Schuster rearrangement.

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