Olefin Cyclopropanations via Sequential Atom Transfer Radical Addition-Dechlorination Reactions

Authors

  • Katrin Thommes Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne
  • Kay Severin

DOI:

https://doi.org/10.2533/chimia.2010.188

Keywords:

Carbocycles, Cyclopropanes, Magnesium, Radicals, Ruthenium

Abstract

In organic synthesis, cyclopropanation reactions are often performed with Simmons–Smith-type reagents or by transition metal catalyzed reactions of olefins with diazo compounds. A novel method for the synthesis of substituted cyclopropanes is described that is based on a two-step reaction sequence. Olefins are reacted with 1,1'-dichlorides in a Ru-catalyzed atom transfer radical addition (ATRA) process and the resulting 1,3-dichlorides are directly converted into cyclopropanes by reductive coupling with magnesium. This one-pot procedure is applicable to a variety of substrates and can be performed in an inter- or intramolecular fashion.

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Published

2010-03-31