Enol functionalized N-heterocyclic carbene lanthanide amide complexes: synthesis, molecular structures and catalytic activity for addition of amines to carbodiimides

LI Zhi; SHEN Qi

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Enol functionalized N-heterocyclic carbene lanthanide amide complexes: synthesis, molecular structures and catalytic activity for addition of amines to carbodiimides

LI Zhi 1,SHEN Qi 2 *

1.College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, JiangSu SuZhou 215123

2.College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou , 215123

*Correspondence author

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Funding: We are grateful to Specialized Research Fund for the Doctoral Program of Higher Education （No.20080285003）

Opened online:22 March 2012

Accepted by: none

Citation: LI Zhi,SHEN Qi.Enol functionalized N-heterocyclic carbene lanthanide amide complexes: synthesis, molecular structures and catalytic activity for addition of amines to carbodiimides[OL]. [22 March 2012] http://en.paper.edu.cn/en_releasepaper/content/4470927

Reaction of anhydrous LnCl3 (Ln = Y, Nd, Sm and Yb) with enol-functionalized imidazolium salt H2LBr (L= 4-OMe-C6H4COCH{C(NCHCHNiPr)}) and NaN(TMS)2 at a molar ratio of 1:4:1 in THF at room temperature afforded the corresponding novel enol-functionalized N-heterocyclic carbene (NHC) lanthanide amides L2LnN(TMS)2 (Ln = Y (1), Nd (2), Sm (3), Yb (4)) in 37-40% yields. Molecular structures of complexes 1-4 were determined by X-ray structure analyses. All these complexes adopt monomeric structures where each 5-coordinated metal is coordinated by two NHC ligands and one amido group.in distorted trigonal bipyramid geometry. These complexes, especially the Yb complex 4 were found to be highly active precatalysts for the catalytic addition of amines to carbodiimides giving guanidines, Complex 4 shows good functional group tolerance and a wide scope of amines including primary and secondary cyclic amines.

Keywords:Enol functionalized N-heterocyclic carbine; Lanthanide; Amide complexes; Catalysis guanylation

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