Abstract
N-heterocyclic carbenes (NHCs) can be easily modified by introducing functional groups at the nitrogen atoms, which leads to versatile coordination chemistry as well as diverse catalytic applications of the resulting complexes. This article summarizes our contributions to the field of NHCs bearing different types of sulfur functions, i.e., thioether, sulfoxide, thiophene, and thiolato. The experimental evidence for the truly hemilabile coordination behavior of a Pd(II) thioether-NHC complex has been reported as well. In addition, complexes bearing rigid CSC-pincer ligands have been synthesized and the reasons for pincer versus pseudo-pincer formation investigated. Incorporation of the electron-rich thiolato function resulted in the isolation of structurally diverse complexes. The catalytic activities of selected complexes have been tested in Suzuki-Miyaura, Mizoroki-Heck and hydroamination reactions.
Highlights
N-heterocyclic carbenes (NHCs) are nowadays ubiquitous ligands in organometallic chemistry as well as catalysis due to their unique properties [1]
In order to evaluate the catalytic activities of Pd(II) complexes bearing sulfur-functionalized NHCs, selected compounds synthesized in our study have been tested in Suzuki-Miyaura, Mizoroki-Heck, and hydroamination reactions
Complexes with more rigid CSCpincer type ligands have been synthesized, and the reasons governing the pincer versus pseudopincer formation have been investigated
Summary
N-heterocyclic carbenes (NHCs) are nowadays ubiquitous ligands in organometallic chemistry as well as catalysis due to their unique properties [1]. Being strong σ-donors and generally weak π-acceptors, NHCs in general form strong bonds with varieties of metal centers, which results in highly stable complexes. Both steric and electronic properties of NHCs can be conveniently tuned by changing the substituents and backbones, which contributes to their popularity. Donor-functionalized NHCs are potentially polydentate ligands, which can give rise to complexes with enhanced stability through ligand chelation. Since carbenes form strong M-C bonds (vide supra), the presence of other donors that form weaker bonds with metal centers makes these polydentate ligands potentially hemilabile. Complexes with different sulfur functions, their structures and catalytic applications
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