Practical Pd/C-Mediated Allylic Substitution in Water
- 7 July 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (16) , 6441-6446
- https://doi.org/10.1021/jo050952t
Abstract
Pd/C-mediated allylic substitution in water is described as an interesting alternative to classical homogeneous conditions. The reaction applied to allylic acetates showed a wide range of compatibility with various nitrogen, sulfur, oxygen, and carbon nucleophiles. Notably, the method features inexpensive reagents and a nontoxic solvent. Moreover, measurement of the palladium content in water by ICP-MS shows low palladium contamination (4 ppm) of the solvent, rendering this method safer for the environment compared to homogeneous conditions. The first asymmetric example of Pd/C-mediated allylic substitution is also disclosed.Keywords
This publication has 11 references indexed in Scilit:
- Water-mediated transition-metal-free Tsuji–Trost-type reactionTetrahedron Letters, 2003
- Suzuki–Miyaura Cross‐Coupling With Quasi‐Heterogeneous PalladiumAdvanced Synthesis & Catalysis, 2003
- Polymer Rings and Chains Consisting of Doubly Silyl-Bridged MetallocenesChemistry – A European Journal, 2002
- Activation of Aryl Chlorides for Suzuki Cross-Coupling by Ligandless, Heterogeneous PalladiumOrganic Letters, 2001
- Catalytic Asymmetric Allylic Alkylation in Water with a Recyclable Amphiphilic Resin-Supported P,N-Chelating Palladium ComplexJournal of the American Chemical Society, 2001
- Heck Reactions of Iodobenzene and Methyl Acrylate with Conventional Supported Palladium Catalysts in the Presence of Organic and/or Inorganic Bases without LigandsChemistry – A European Journal, 2000
- Allylic substitution in water catalyzed by amphiphilic resin-supported palladium-phosphine complexesTetrahedron, 1999
- Electron nuclear double resonance (ENDOR) of metalloenzymesAccounts of Chemical Research, 1991
- Palladium catalyzed c-allylation of highly acidic carbo and heterocyclic β-dicarbonyl compoundsTetrahedron, 1988
- The Trialkylborane-initiated Graft Copolymerization of Methyl Methacrylate onto HemoglobinBulletin of the Chemical Society of Japan, 1971