The Lewis acid promoted allylation of aldehydes has become an important carbon-carbon bond forming reaction in organic chemistry. In this context, we have developed an alternative over existing catalytic processes, wherein aldehydes are subject in acetonitrile to reaction of allylation with allyltributylstannane in the presence of 1.0 equiv of cerium(III) chloride heptahydrate (CeCl3.7H2O), an inexpensive and mild Lewis acid. The allylation has been accelerated by using an inorganic iodide as a cocatalyst, and various iodide salts were examined. The procedure must use allylstannane reagent instead of allylsilane reagent, desirable for environmental reasons, but high chemoselectivity was observed, and this is opposite the results obtained with other classical Lewis acids such as TiCl4 and Et2O.BF3.
G. Bartoli, M. Bosco, A. Giuliani, E. Marcantoni, A. Palmieri, M. Petrini, et al. (2004). Investigation into the Allylation Reactions of Aldehydes Promoted by the CeCl3.7H2O-NaI System as a Lewis Acid. JOURNAL OF ORGANIC CHEMISTRY, 69, 1290-1297 [10.1021/jo035542o].
Investigation into the Allylation Reactions of Aldehydes Promoted by the CeCl3.7H2O-NaI System as a Lewis Acid
BARTOLI, GIUSEPPE;BOSCO, MARCELLA;SAMBRI, LETIZIA
2004
Abstract
The Lewis acid promoted allylation of aldehydes has become an important carbon-carbon bond forming reaction in organic chemistry. In this context, we have developed an alternative over existing catalytic processes, wherein aldehydes are subject in acetonitrile to reaction of allylation with allyltributylstannane in the presence of 1.0 equiv of cerium(III) chloride heptahydrate (CeCl3.7H2O), an inexpensive and mild Lewis acid. The allylation has been accelerated by using an inorganic iodide as a cocatalyst, and various iodide salts were examined. The procedure must use allylstannane reagent instead of allylsilane reagent, desirable for environmental reasons, but high chemoselectivity was observed, and this is opposite the results obtained with other classical Lewis acids such as TiCl4 and Et2O.BF3.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
