Conversion of pentynol to pentanone catalysed by Pd(II) metal centres |
| |
| Authors: | M. Fernanda N.N. Carvalho Ana S.D. Ferreira |
| |
| Affiliation: | a Centro de Qu?´mica Estrutural, Complexo I, Instituto Superior Técnico, Av. Rovisco Pais 1049-001 Lisboa, Portugal
b Institut für Physik, Universität Augsburg, Universitätsstr. 1, 86159 Augsburg, Germany |
| |
| Abstract: | The cyclization of 3- or 4-pentyn-1-ol is catalysed by PdCl2 or trans-[PdCl2L2] (L = R-camphorimine; R = Ph; Pri; NMe2) complexes at room temperature affording heterocyclic compounds, respectively, 2-methyl-2-pent-3-ynyloxy-tetrahydrofuran or 2-methyl-2-pent-4-ynyloxy-tetrahydrofuran which subsequently add water to give selectively 5-(2-methyl-tetrahydrofuran-2-yloxy)-pentan-2-one from both starting materials. By hydrolysis 5-(2-methyl-tetrahydrofuran-2-yloxy)-pentan-2-one undergoes ring cleavage to form 5-hydroxy-2-pentanone. The catalytic activity and selectivity of complexes trans-[PdCl2L2] (L = R-camphorimine) depend on the characteristics of the R group (NMe2 > Pri > Ph). The catalytic activity of PdCl2 is comparable to that of trans-[PdCl2L2] (L = Ph-camphorimine) which is the less efficient catalyst. |
| |
| Keywords: | Catalysis Alkynols Palladium Camphor Heterocycles Organic synthesis |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
