Fe(0)-Mediated Synthesis of Tri- and Tetra-Substituted Olefins from Carbonyls: An Environmentally Friendly Alternative to Cr(II)

J. R. Falck,*† Romain Bejot,‡ Deb K. Barma,† Anish Bandyopadhyay,† Suju Joseph,† and Charles Mioskowski*‡;
Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390, and Laboratoire de Synthèse Bio-Organique, UMR 7175-LC1, Faculté de Pharmacie, Université Louis Pasteur, 74 Route du Rhin, BP 24, 67 401 Illkirch, France
J. Org. Chem., 2006, 71 (21), pp 8178–8182
DOI: 10.1021/jo061445u
Publication Date (Web): September 13, 2006
Copyright © 2006 American Chemical Society

Abstract

Abstract Image

Fe(0) was investigated as a cost-effective, environmentally friendly alternative to Cr(II) for the olefination of carbonyls by activated polyhalides. In many instances, Fe(0) was equivalent or superior to Cr(II). Notably, Fe(0), but not Cr(II), proved compatible with a wide range of functionality, inter alia, unprotected phenol, aryl nitro, carboxylic acid, and alkyl nitrile. A surprising reversal of stereoselectivity for aldehydes versus ketones was observed using both metals. The resultant α-halo-α,β-unsaturated or α,β-unsaturated carboxylic acids, esters, and nitriles are common structural elements in numerous compounds of interest as well as key intermediates in the preparation of other functionality.

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History

  • Published In Issue October 13, 2006
  • Received July 11, 2006

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