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.
Dehydrogenative Meyer–Schuster-Like Rearrangement: A Gold-Catalyzed Reaction Generating an Alkyne†
Article first published online: 11 DEC 2013
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 53, Issue 4, pages 1144–1147, January 20, 2014
How to Cite
Yu, Y., Yang, W., Pflästerer, D. and Hashmi, A. S. K. (2014), Dehydrogenative Meyer–Schuster-Like Rearrangement: A Gold-Catalyzed Reaction Generating an Alkyne. Angew. Chem. Int. Ed., 53: 1144–1147. doi: 10.1002/anie.201307647
- Issue published online: 21 JAN 2014
- Article first published online: 11 DEC 2013
- Manuscript Received: 30 AUG 2013
- hypervalent iodine
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.