173035-10-4

Usage

Uses

1. Used as a Precursor to N-heterocyclic Carbene Catalysts for various applications in the field of organic chemistry.
Used in Organic Chemistry:
1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE is used as a Precursor to N-heterocyclic Carbene Catalysts for the following reasons:
A regioselective cycloaddition of terminal acetylenes with azides, leading to 1,4-disubstituted triazoles. Internal acetylenes can also be used with this catalyst.
Markovnikov-type hydration of terminal alkynes.
Hydrosilylation of ketones.
Cycloaddition of azides and alkynes.
Suzuki-Miyaura reactions.
Luminescence experiments.

InChI:InChI=1/C21H28N2.ClH/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6;/h9-12H,7-8,13H2,1-6H3;1H

Upstream product

• 75-09-2 dichloromethane 
• 173035-11-5 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene 
• 107-06-2 1,2-dichloro-ethane 
• 122-51-0 orthoformic acid triethyl ester 
• 88-05-1 2,4,6-trimethylaniline 
• 75105-48-5 N,N'-dimesitylformamidine 
• 1181444-57-4 N-(2-iodoethyl)-2,6-dimethylbenzenaminium chloride 
• 258278-23-8 N¹,N²-dimesitylethane-1,2-diaminium chloride 
• 79354-30-6 2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid ethyl ester 
• 91325-46-1 N,N′-bis(2,4,6-trimethylphenyl)oxalamide 
• 64-18-6 formic acid 
• 75105-48-5 N,N'-bis(2,4,6-trimethylphenyl)formamidine 
• 56222-36-7 N,N'-bis(2,4,6-trimethylphenyl)ethanediimine 
• 67565-93-9 N-(diphenyl methylene)-2,4,6-trimethylaniline 

Downstream Products

• 258278-26-1 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene 
• 465543-02-6 2-ethoxy-1,3-bis[(2,4,6-trimethyl)phenyl]imidazolidine 
• 947742-60-1 1,3-bis(2,4,6-trimethylphenyl)-2-N-phenylthiocarbamoyl imidazolinium salt 
• 260054-47-5 1,3-bis(2,4,6-trimethylphenyl)-2-(trichloromethyl)imidazolidine 
• 246047-72-3 (1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)(PCy₃)Cl₂Ru=CHPh 
• 246047-72-3 tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride 
• 587833-64-5 (1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)bis(η5-cyclopentadienyl)molybdenum 

Relevant academic research and scientific papers

Highly efficient palladacycle/dihydroimidazolium chloride system for the suzuki-miyaura cross-coupling of aryl halides (I, Br, Cl) with arylboronic acids

A combination of a tertiary amine-based palladacycle and an N-heterocyclic carbene ligand precursor (1, N,N-bis-mesityl-4,5-dihydroimidazolium chloride) has been applied to catalyze the Suzuki-Miyaura cross-coupling of aryl halides with arylboronic acids. The substrate scope is general: a variety of electron rich and deficient aryl halides (I, Br, Cl) and arylboronic acids were found to undergo the cross-coupling reaction in good to excellent yields at low catalyst loading of 0.01-1 mol%. A combination of a tertiary amine-based palladacycle and an N-heterocyclic carbene ligand precursor has been applied to catalyze the Suzuki-Miyaura cross-coupling of aryl halides with arylboronic acids. Varieties of electron rich and deficient aryl halides (I, Br, Cl) and arylboronic acids were found to undergo the cross-coupling reaction in good to excellent yields at low catalyst loading of 0.01-1 mol%.

An air stable carbene and mixed carbene 'dimers'

The air-stable crystalline carbene 1,3-dimesityl-4,5-dichloroimidazol- 2-ylidene (2) is produced from the chlorination of 1,3-dimesityimidazol-2- ylidene (1) by 2 equiv of carbon tetrachloride. The physical and spectroscopic properties of the carbene are

Application of Quantitative 1H and 19F NMR to Organometallics

Purity assessment of organometallics is particularly important for catalytic applications. While quantitative NMR is a well-known method in pharmaceutic chemistry, the present work illustrates its usefulness for the determination of the ligands and organometallics purities using proton and fluorine NMR. This method is fast, straightforward and provides accuracy results.

Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors

A novel and efficient approach to the synthesis of 2-vinylbenzylamines is reported. This involves obtaining 2-vinylbenzylamine ligands from tetrahydroisoquinoline by alkylation and reduction followed by the Hofmann cleavage. The resultant 2-vinylbenzyl-amines allowed us to obtain new Hoveyda–Grubbs catalysts, which were thoroughly characterised by NMR, ESIMS, and X-ray crystallography. The utility of this chemistry is further demonstrated by the tests of the novel catalysts (up to 10?2 mol %) in different metathesis reactions such as cross metathesis (CM), ring-closing metathesis (RCM) and ring-opening cross metathesis (ROCM).

Catalytic hydrogenation of α,β-unsaturated carboxylic acid derivatives using copper(i)/N-heterocyclic carbene complexes

A simple and air-stable copper(i)/N-heterocyclic carbene complex enables the catalytic hydrogenation of enoates and enamides, hitherto unreactive substrates employing homogeneous copper catalysis and H2 as a terminal reducing agent. This atom economic transformation replaces commonly employed hydrosilanes and can also be carried out in an asymmetric fashion.

Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts

The invention pertains to the use of Group 8 transition metal carbene complexes as catalysts for olefin cross-metathesis reactions. In particular, ruthenium and osmium alkylidene complexes substituted with an N-heterocyclic carbene ligand are used to catalyze cross-metathesis reactions to provide a variety of substituted and functionalized olefins, including phosphonate-substituted olefins, directly halogenated olefins, 1,1,2-trisubstituted olefins, and quaternary allylic olefins. The invention further provides a method for creating functional diversity using the aforementioned complexes to catalyze cross-metathesis reactions of a first olefinic reactant, which may or may not be substituted with a functional group, with each of a plurality of different olefinic reactants, which may or may not be substituted with functional groups, to give a plurality of structurally distinct olefinic products. The methodology of the invention is also useful in facilitating the stereoselective synthesis of 1,2-disubstituted olefins in the cis configuration.

Improved microwave synthesis of unsymmetrical N,N'-diaryl-1,2-aminoethane and imidazolidinium salts as precursors of N-heterocyclic carbenes

Lithium aluminium hydride reduction of bis-unsymmetric-diaryloxamides 3 is difficult to accomplish especially for the sterically hindered mesityl derivative. Using microwaves LAH reduction of 3a,d was successful in a short time, however, with cleavage of the ether linkage to give compounds 11a,d. Extension of this method enabled the reduction of bis-oxamide derivatives 13 to the corresponding tetraamine derivative 14 which was then converted to the bis-imidazolidinium salt 15. Application of this method led to rapid reduction of unsymmetric N,N'-diaryloxamides 16 to the corresponding N,N'- diarylethylenediamines 17 which were converted to their corresponding imidazolidinium salts 18. the Partner Organisations 2014.

Continuous synthesis and use of N-heterocyclic carbene copper(I) complexes from insoluble Cu2O

It is demonstrated that homogeneous N-heterocyclic carbene-copper(I)- chloride complexes can be prepared continuously by flowing NHC precursors through a packed bed of solid Cu2O suspended in molecular sieves. The method enables the synthesis o

Oxygen-atom insertion of NHCecopper complex: The source of oxygen from N, N-dimethylformamide

An unprecedented protocol for oxygen-atom insertion reaction of NHCecopper complexes has been developed by employing N,N-dimethylformamide as the oxygen source, which allows the preparation of imidazolinones from carbene complexes and decodes one of the m

A direct and practical approach for the synthesis of N-heterocyclic carbene coinage metal complexes

A novel direct and practical synthetic route leading to N-heterocyclic carbene coinage metal complexes has been developed by using air stable, commercial available Au(III) salt [MAuCl4·2H2O], CuCln (n=1,2) or AgCl, and imidazolium salts as starting materials. The reaction proceeded without sacrificing carbene transfer agent (Ag 2O) or using highly sensitive free NHC.