Palladium(0) pre-catalysts with heteroditopic NHC-amine ligands by transmetallation from their silver(I) complexes

The synthesis of an air‐stable series of Pd0 complexes with dissymmetric bidentate N‐heterocyclic carbene–amine ligands has been performed. The key step is an unprecedented carbene transfer from AgI to obtain electron‐rich zero‐valent palladium precatalysts. The coordination behavior of the ligands...

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Bibliographic Details
Published in:Applied organometallic chemistry 2009-06, Vol.23 (6), p.225-228
Main Authors: Warsink, Stefan, Hauwert, Peter, Siegler, Maxime A., Spek, Anthony L., Elsevier, Cornelis J.
Format: Article
Language:English
Subjects:
carbene complexes
organometallic compounds
palladium
silver
transmetallation
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Summary:The synthesis of an air‐stable series of Pd0 complexes with dissymmetric bidentate N‐heterocyclic carbene–amine ligands has been performed. The key step is an unprecedented carbene transfer from AgI to obtain electron‐rich zero‐valent palladium precatalysts. The coordination behavior of the ligands was determined with X‐ray crystallography. Surprising results were obtained in the catalysis of transfer semi‐hydrogenation, where the addition of base appeared not to be necessary to obtain the desired product stereoselectively. Copyright © 2009 John Wiley & Sons, Ltd. First transfer of NHC from AgI to a zero‐valent transition metal: the synthesis of an air‐stable series of Pd0 complexes with dissymmetric bidentate N‐heterocyclic carbene‐amine ligands has been performed. The key step is an unprecedented carbene transfer from AgI to Pd0 to obtain electron‐rich zerovalent palladium compounds in which the carbene and the amine functionality are both coordinated. Their structure was determined by X‐ray crystallography. Excellent results were obtained when using these compounds as precatalysts for the transfer semi‐hydrogenation of alkynes.
ISSN:0268-2605
1099-0739
DOI:10.1002/aoc.1501