874184-69-7

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 870123-99-2 N,N'-bis(2,6-dimethyl-4-bromophenyl)ethylenediamine 
• 24596-19-8 4-bromo-2,6-dimethylphenylamine 
• 1351288-11-3 N,N’-bis(4-bromo-2,6-dimethylphenyl)formimidamide 
• 107-06-2 1,2-dichloro-ethane 

Downstream Products

• 1434880-46-2 1,3-bis(4-bromo-2,6-dimethylphenyl)-4,5-dihydro-1H-imidazol-3-ium-2-carboxylate 

Relevant academic research and scientific papers

π-face donor properties of N-heterocyclic carbenes

The donor properties of aryl substituted N-heterocyclic carbenes are characterized by lone pair donation from the carbene carbon and, as is shown here, by donation of electron density of the aromatic π-face of the NHC aryl groups towards the metal. The Royal Society of Chemistry 2005.

ARTICLES AND METHODS COMPRISING PERSISTENT CARBENES AND RELATED COMPOSITIONS

Articles and methods comprising persistent carbenes are provided, as well as related compositions. In some embodiments, a persistent carbene may be associated with a portion of a substrate (e.g., at least a portion of a surface on the substrate). In certain embodiments, the association of persistent carbene with the substrate may be used to affect certain properties of substrate (e.g., surface chemistry, stability). In some cases, a persistent carbene may be functionalized after association with a portion of a substrate. In some embodiments, a persistent carbene and at least one secondary compound may be associated with a portion of a substrate. Articles and methods of the present invention may be useful for applications involving electronics, sensing, microfabrication, nanotechnology, biomimetic, and drug delivery, amongst others.

Addressable carbene anchors for gold surfaces

New strategies to access functional monolayers could augment current surface modification methods. Here we present addressable N-heterocyclic carbene (ANHC) anchors for gold surfaces. A suite of experimental and theoretical methods was used to characteriz

Switched stereocontrol in Grubbs - Hoveyda complex catalyzed ROMP utilizing proton-switched NHC ligands

Grubbs-Hoveyda and Grubbs III type complexes with ferrocenyl- or -NEt 2-substituted NHC ligands were synthesized according to standard procedures. The electron donation of the NHC ligands in the respective ruthenium complexes can be modulated by oxidation of the ferrocenyl moiety or by protonation of the amino group. The neutral and the respective cationic (oxidized or protonated) ruthenium complexes were tested in the ROMP of norbornene. The change in the electron donation of the NHC ligands upon protonation leads to a significant change in the double-bond geometry (from E/Z ratio = 0.78 to E/Z = 1.04) and in the microstructure of the resulting polynorbornene. Consequently, addition of acid and protonation of the living catalyst attached to the polymer chain during the polymerization reaction allows fine-tuning the E/Z ratio of the resulting polynorbornene.

Tuning the electronic properties of N-heterocyclic carbenes

The electron-donating properties of N-heterocyclic carbenes ([N,N′-bis(2,6-dimethylphenyl)imidazol]-2-ylidene and the respective dihydro ligands) with 4,4′-R-substituted aryl rings (4,4′-R = NEt2, OC12H25, Me, H, Br, S(4-t

1,3-Diarylimidazolidin-2-ylidene (NHC) complexes of Pd(II): Electronic effects on cross-coupling reactions and thermal decompositions

The synthesis of 1,3-diarylimidazolidin-2-ylidene (NHC) precursor, 1,3-bis(2,4,6-trimethylphenyl)imidazolinium chloride, (3b) has been extended to the electronically and sterically modified NHC precursors 3a (X = H), 3c (X = Br) and 3e (X = Cl) in order t

Microwave-assisted synthesis of N-heterocyclic carbene precursors

A very simple and efficient procedure is reported for the synthesis of 1,3-diarylimidazolinium chlorides by cyclization of N,N′- diarylethylenediamines dihydrochlorides with triethyl orthoformate under microwave irradiation. Georg Thieme Verlag Stuttgart.

Redox-switchable phase tags for recycling of homogeneous catalysts

(Chemical Equation Presented) A homogeneous catalytic complex is tagged with two ferrocenyl groups to control its solubility properties by reversible switching between its neutral and dicationic states (see scheme). This approach is carried out on an olefin-metathesis catalyst and is shown to effectively switch its catalytic activity on and off; furthermore, efficient separation of the catalyst from the reaction products and subsequent recycling of the catalyst is possible.