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Stereoselective hydrogenation of terpenes using platinum-based catalysts

Paper ID Volume ID Publish Year Pages File Format Full-Text
44060 46002 2007 8 PDF Available
Title
Stereoselective hydrogenation of terpenes using platinum-based catalysts
Abstract

In the present paper, the catalytic hydrogenation of some terpenes is discussed. Catalysts employed were silica supported Pt and Pt modified by tin addition using techniques derived from surface organometallic chemistry on metals. Selected substrates were α-pinene, verbanone, fenchone, camphor and verbenone. The catalytic systems studied allow the control of reaction stereoselectivity. The hydrogenation of α-pinene led selectively to cis-pinane, and it was possible to observe that the modification of Pt/SiO2 with Sn caused an important decrease of the catalytic activity; this fact can be explained by combined electronic and geometrical effects. In sterically hindered terpenones (fenchone and camphor), the topography of the molecule resulted of fundamental importance in controlling the stereoselectivity of the reaction. In verbenone hydrogenation, the Pt/SiO2 catalyst allowed to obtain cis-verbanone with high yield and catalysts modified with Sn led to the formation of a principal product (cis-verbanol) different than the one obtained by chemical reduction with NaBH4 (cis-verbenol).

Graphical abstractThe catalytic hydrogenation of some terpenes is discussed. Catalysts employed were silica supported Pt and Pt modified by tin addition. Selected substrates were α-pinene, verbanone, fenchone, camphor and verbenone. The catalytic systems studied allow the control of reaction stereoselectivity. In sterically hindered terpenones, the topography of the molecule resulted of fundamental importance in controlling the stereoselectivity of the reaction. Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Platinum–tin catalysts; Surface organometallic chemistry; Hydrogenation; Stereoselectivity; α-Pinene; Camphor; Verbenone
First Page Preview
Stereoselective hydrogenation of terpenes using platinum-based catalysts
Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 318, 20 February 2007, Pages 1–8
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis