Progress of the Barton-McComble Methodology: From tin hydrides to Silanes

Abstract

Use of organosilanes that promote the Barton-McCombie deoxygenation is an emerging methodology for organic transformations. A comparison between a variety of substituted silanes is presented. (Me3Si)3SiH rivals Bu3SnH in efficiency and it is a superior reagent from ecological and practical perspectives.

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    Note added in proofi We thank Professor D.H.R. Barton for kindly sending us a copy of his recent book (D.H.R. Barton and S.I. Parekh, Half a Century of Free Radical Chemistry, Cambridge University Press, 1993), in which he describes some of his inventions of radical reactions. In this book, chapter 4 is dedicated to the topic of deoxygenation reaction and we found the anecdote reported on the discovery of this reaction amusing. In chapter 6 S.I. Parekh reported some recent examples of the applications of the Barton-McCombie methodology.

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Correspondence to C. Chatgilialoglu or C. Ferreri.

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Chatgilialoglu, C., Ferreri, C. Progress of the Barton-McComble Methodology: From tin hydrides to Silanes. Res Chem Intermed 19, 755–775 (1993). https://doi.org/10.1163/156856793X00361

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Keywords

  • Xanthate
  • Radical Chain Reaction
  • Deuteride
  • Thiocarbonyl
  • Methyl Elaidate