Issue 7, 2000
From the journal:

Journal of the Chemical Society, Dalton Transactions

Binaphthyl Schiff base complexes of palladium(II). Structures and reactivities toward alkeneepoxidation

Xiang-Ge Zhou,a   Jie-Sheng Huang,a   Xiao-Qi Yu,a   Zhong-Yuan Zhoua  and  Chi-Ming Che*a  

* Corresponding authors

a Department of Chemistry, The University of Hong Kong, Pokfulam Road, HongKong
E-mail: cmche@hkucc.hku.hk

b Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China

Abstract

Palladium(II) binaphthyl Schiff base complexes [PdII(L)] (1: H2L = (racemic or R)-2,2′-bis(3,5-dichloro-2-hydroxybenzylideneamino)-1,1′-binaphthyl (H2L2); 2: H2L = (R)-2,2′-bis(3,5-dichloro-2-hydroxylbenzylideneamino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl (H2L3)) were prepared from sequential reactions of H2L with sodium methoxide and palladium(II) acetate in methanol in about 70% yields. Both complexes 1 and 2 have been characterised by X-ray crystallography as well as 1H NMR, IR, UV/VIS and MS spectroscopy. The structures of 1 and 2 feature a pseudo planar N2O2 arrangement with the Schiff base ligands adopting a stepped conformation, in contrast to the non-planar N2O2 geometry usually observed for this type of Schiff base bound to various metal ions. The catalytic behaviour of complexes 1 and 2 toward asymmetric epoxidation of styrenes was investigated. With 2 as a catalyst, a 71% ee was obtained for the epoxidation of p-fluorostyrene by tBuOOH.

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Article information

DOI
https://doi.org/10.1039/A908917I
Article type
Paper
Submitted
09 Nov 1999
Accepted
31 Jan 2000
First published
09 Mar 2000

J. Chem. Soc., Dalton Trans., 2000, 1075-1080

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Binaphthyl Schiff base complexes of palladium(II). Structures and reactivities toward alkene epoxidation

X. Zhou, J. Huang, X. Yu, Z. Zhou and C. Che, J. Chem. Soc., Dalton Trans., 2000, 1075 DOI: 10.1039/A908917I

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