Synthesis of trisubstituted alkenes via direct oxidative arene-alkene coupling.
J Org Chem
; 78(16): 8044-53, 2013 Aug 16.
Article
em En
| MEDLINE
| ID: mdl-23841693
ABSTRACT
The use of an inorganic oxidant with an acetic acid/acetonitrile solvent combination has been identified as optimal for direct arene/1,2-disubstituted alkene oxidative couplings, providing an efficient route to trisubstituted alkenes. The acetonitrile cosolvent dramatically accelerates the rate of reaction, and an insoluble inorganic oxidant limits unwanted oxidation of substrates. The scope of this procedure is illustrated with arenes and alkenes containing electron-donating and -withdrawing substituents resulting in a general synthetic strategy to trisubstituted alkenes. In situ ESI-MS analysis of the reaction components has identified the key Pd intermediates in the Fujiwara-Moritani catalytic cycle.
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01-internacional
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MEDLINE
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Alcenos
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article