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Synthesis 2009(16): 2674-2678  
DOI: 10.1055/s-0029-1216895
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Bimetallic Palladium-Platinum-on-Carbon-Catalyzed H-D Exchange Reaction: Synergistic Effect on Multiple Deuterium Incorporation

Tomohiro Maegawaa,1, Nobuhiro Itob, Keiji Oonob, Yasunari Monguchia, Hironao Sajiki*a
a Laboratory of Organic Chemistry, Department of Organic and Medicinal Chemistry, Gifu Pharmaceutical University, Gifu 502-8585, Japan
b Chemical Products Research Laboratories, Wako Pure Chemical Industries, Ltd., Matoba, Kawagoe 350-1101, Japan
Fax: +81(58)2375979; e-Mail: sajiki@gifu-pu.ac.jp;
Further Information

Publication History

Received 12 February 2009
Publication Date:
10 July 2009 (online)

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Abstract

We prepared several activated carbon-supported bimetallic Pd-Pt catalysts (Pd-Pt/C) by using various reducing reagents, and examined their catalytic activities for the deuteration of alkyl-substituted aromatic compounds. Multiple deuterations catalyzed by Pt-Pd/C proceeded in D2O at 180 ˚C under a H2 atmosphere, and a synergistic effect was observed in relation to the incorporation of deuterium at sterically hindered positions on aromatic rings.

Key words

heterogeneous catalysis - palladium - platinum - H-D exchange - synergy - bimetallic

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1

Present address: Graduate School of Pharmaceutical Sciences, Osaka University, Suita Osaka, 565-0871, Japan.

12

The Pt and Pd contents of 5% Pd-Pt/C(NaBH4) were almost equal (Pd, 3.6%; Pt, 3.5% by ICP-AES), whereas 5% Pd-Pt/C(H2), 5% Pd-Pt/C(NH2NH2), and 5% Pd-Pt/C(HCHO) showed higher contents of Pd than of Pd (Pd, 3.9-4.1%; Pt, 2.7-2.8%).