Efficient Metal-Catalyzed Direct Benzylation and Allylic Alkylation of 2,4-Pentanediones

Magnus Rueping,* Boris J. Nachtsheim, and Alexander Kuenkel
Degussa Endowed Professorship, Institute of Organic Chemistry & Chemical Biology, Johann-Wolfgang Goethe University Frankfurt am Main, Max-von-Laue-Str. 7, D-60438 Frankfurt, Germany
Org. Lett., 2007, 9 (5), pp 825–828
DOI: 10.1021/ol063048b
Publication Date (Web): January 31, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, m.rueping@chemie.uni-frankfurt.de

Abstract

Abstract Image

A highly effective metal-catalyzed benzylation and allylic alkylation of 2,4-pentanediones has been developed. This new bismuth-catalyzed direct carbon−carbon bond forming reaction provides the corresponding monoalkylated dicarbonyl compounds in high yields after short reaction times using the lowest amounts of catalyst (1 mol %) and the free alcohol. In addition, a new route to substituted indenes is presented.

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History

  • Published In Issue March 01, 2007
  • Received December 17, 2006

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