Radical‐Mediated Three‐Component Coupling of Alkenes | Zendy

Schaffner Arnaud Pierre | Zendy; Sarkunam Kandhasamy | Zendy; Renaud Philippe | Zendy

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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.

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