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Radical‐Mediated Three‐Component Coupling of Alkenes
Author(s) -
Schaffner Arnaud Pierre,
Sarkunam Kandhasamy,
Renaud Philippe
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690225
Subject(s) - chemistry , hydroboration , alkene , radical , allylic rearrangement , electrophile , adduct , tandem , sulfone , coupling (piping) , conjugate , medicinal chemistry , organic chemistry , catalysis , mechanical engineering , mathematical analysis , materials science , mathematics , engineering , composite material
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.