Olefin Cyclopropanations via Sequential Atom Transfer Radical Addition-Dechlorination Reactions

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.


Published in:
Chimia, 64, 188-190
Year:
2010
Keywords:
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 Record created 2011-12-16, last modified 2018-09-13


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