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.
Keywords: Carbocycles ; Cyclopropanes ; Magnesium ; Radicals ; Ruthenium ; Kharasch Addition ; Controlled Polymerization ; Cyclization Reactions ; Catalyst Precursors ; Gaba(C) Receptors ; Copper-Complexes ; Reducing Agent ; Atrc Reactions ; Rucl(Cp-Asterisk)(Pph3)(2) ; Reactivity
Record created on 2011-12-16, modified on 2016-08-09