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Dehydrogenative Meyer-Schuster-Like Rearrangement: A Gold-Catalyzed Reaction Generating an Alkyne
Journal article   Peer reviewed

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

Yang Yu, Weibo Yang, Daniel Pflaesterer and A. Stephen K. Hashmi
Angewandte Chemie (International ed.), Vol.53(4), pp.1144-1147
20/01/2014
PMID: 24338996

Abstract

Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology
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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