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2005
C-C bond formation
O 0282
Superacidic Activation of α,β-Unsaturated Amides and Their Electrophilic Reac— Direct, superacid-induced one-step reactions between α,β-unsaturated amides
03- 067 tions.
and weak aromatic nucleophiles such as arenes give the corresponding β-arylpropionamides in yields up to 100%. While AlCl3 induces clean reactions in the most cases,
triflic acid is shown to be generally less applicable. Some amides also undergo selective
ionic hydrogenation with cyclohexane to give saturated amides such as (XI). The direct
observation of a dicationic species as superelectrophile is observed by low-temperature
NMR. — (KOLTUNOV*, K. Y.; WALSPURGER, S.; SOMMER, J.; Eur. J. Org.
Chem. 2004, 19, 4039-4047; Lab. Physicochim. Hydrocarbures, Cent. Rech. Chim.,
Univ. Louis Pasteur, F-67008 Strasbourg, Fr.; Eng.) — Kieslich
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