Helvetica Chimica Acta · 2006 · 24 citations · 15 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCross-coupling ReactionsOrganic SynthesisRadical ReactionsConjugate AdditionRadical Cascade ReactionsRadical Reaction MechanismsSelective Coupling
Abstract A tandem radical process involving conjugate addition to an activated alkene followed by allylation is reported. B ‐Alkylcatecholboranes, easily available via hydroboration of the corresponding alkenes, were used to generate the initial radicals. These radicals add efficiently to electrophilic alkenes such as phenyl vinyl sulfone, N ‐phenylmaleimide, and dialkyl fumarate. In the last step of this one‐pot process, the radical adducts react with the allylic sulfones. The whole process can be considered as a unique and selective coupling of three different alkenes.
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Tin Hydride Substitutes in Reductive Radical Chain Reactions
Armido Studer, Stephan Amrein · Synthesis · 2002 · 221 citations