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Dehydrogenative Meyer-Schuster-like rearrangement: a gold-catalyzed reaction generating an alkyne.

Authors
  • Yu, Yang1
  • Yang, Weibo
  • Pflästerer, Daniel
  • Hashmi, A Stephen K
  • 1 Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany) http://www.hashmi.de. , (Germany)
Type
Published Article
Journal
Angewandte Chemie International Edition in English
Publisher
Wiley (John Wiley & Sons)
Publication Date
Jan 20, 2014
Volume
53
Issue
4
Pages
1144–1147
Identifiers
DOI: 10.1002/anie.201307647
PMID: 24338996
Source
Medline
Keywords
License
Unknown

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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