Pd(OAc)2 in combination with P(t-Bu)3 catalyzes the coupling of b-methallyl alcohol with 1-bromo-3,4-(methylenedioxy)benzene (1a), 1-bromo-4-methoxybenzene (1b), or 1-bromo-4-tert-butylbenzene (1c). The reaction affords the corresponding 2-methyl-3-aryl-propanals, which are valuable floral fragrances. With 1a or 1b high reaction rates are obtained at 130 C using NMP/water mixtures and an inorganic base such as Na2CO3. The chemoselectivity of the reaction is almost complete, so that the process appears practically feasible. In contrast, the coupling of b-methallyl alcohol with 1c proceeds with low reaction rates.
Autori: | |
Data di pubblicazione: | 2008 |
Titolo: | Arylation of β-methallyl alcohol catalyzed by Pd(OAc)2 in combination with P(t-Bu)3: application to fragrance synthesis |
Rivista: | TETRAHEDRON |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tet.2007.11.019 |
Volume: | 64 |
Appare nelle tipologie: | 2.1 Articolo su rivista |
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