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Environmentally-benign palladium(II)-exchanged hydroxyapatite-catalyzed allylic alkylation of allyl methyl carbonate in water

Paper ID Volume ID Publish Year Pages File Format Full-Text
41792 45900 2010 6 PDF Available
Title
Environmentally-benign palladium(II)-exchanged hydroxyapatite-catalyzed allylic alkylation of allyl methyl carbonate in water
Abstract

Palladium(II)-exchanged hydroxyapatite (PdHAP; for example, PdHAP-B has a Pd/Ca ratio = ca 1/200) was prepared by ion-exchanging with Ca2+ from calcined hydroxyapatite and Pd(NO3)2 in water at 70 °C for 24 h. The ion-exchange was revealed by inductively coupled plasma analysis; Pd2+ was almost absent in any filtrate that included over 1.6 equimolar amounts of Ca2+ relative to the amount of Pd2+ consumed. The PdHAP (1 mol% Pd) functioned as a catalyst for the allylic alkylation of allyl methyl carbonate with active methylene compounds such as diethyl malonate, 2-ethoxycarbonylcyclopentanone, 2-ethoxycarbonylcyclohexanone, and 2,2-dimethyl-1,3-dioxane-4,6-dione at 50 °C in water under air. Over 97% of the PdHAP was recovered by centrifugation followed by decantation, and the material could be reused. The catalytic activity of PdHAP accompanied by satisfactory yields of monoallylated products was maintained in ten repetitive uses for the allylic alkylation of allyl methyl carbonate with diethyl malonate at 50 °C for 24 h in water under air. From the standpoints of yield and handling, using water as a solvent was superior to using an organic medium such as ethanol, THF or DMF. Thus, this heterogeneous PdHAP-catalyzed allylic alkylation will be one of the environmentally-benign organic syntheses.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (49 K)Download as PowerPoint slideResearch highlights▶ Environmentally-benign heterogeneous catalytic process in organic synthesis. ▶ Environmentally-benign organic synthesis in water. ▶ Palladium-exchanged hydroxyapatite-catalyzed allylic alkylation in water. ▶ Repetitively-usable palladium-exchanged hydroxyapatite catalyst in water.

Keywords
Palladium; Hydroxyapatite; Heterogeneous catalysis; Water medium; Allylic alkylation
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Environmentally-benign palladium(II)-exchanged hydroxyapatite-catalyzed allylic alkylation of allyl methyl carbonate in water
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 387, Issues 1–2, 20 October 2010, Pages 107–112
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us