578743-87-0

Usage

Uses

Used in Pharmaceutical Industry:
CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) is used as a catalyst for the reduction of olefins and carbonyl compounds, which are key steps in the synthesis of various pharmaceutical compounds. Its ability to facilitate these reactions with high selectivity and efficiency makes it a valuable tool in the development of new drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) is employed as a catalyst for carbene transfer reactions, aziridination of olefins, and methyleneation of aldehydes. These reactions are essential for the construction of complex molecular structures, and the use of this copper complex allows for greater control over the reaction outcomes, leading to the synthesis of a wide range of organic compounds with potential applications in various industries.
Used in Material Science:
CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) can also be utilized in the development of new materials, such as polymers and coordination compounds, due to its unique catalytic properties. Its ability to participate in various chemical reactions can lead to the creation of novel materials with enhanced properties, such as improved stability, reactivity, or selectivity, which can be applied in various technological applications.

Reaction

Catalyst for the aziridination of olefins. Mild catalyst, superior to CuCl, in the methylenetriphenylphosphorane methyleneation of aldehydes and ketones. Copper(I) catalyzed alkylation of aryl and alkenylsilanes. Copper-catalyzed formal methylative and hydrogenative carboxylation of alkynes with carbon dioxide. Regioselective copper-catalyzed carboxylation of allylboronates with carbon dioxide. Carboxylation of organoboronic esters with potassium methyl carbonate under copper catalysis. Catalytic anti-Markovnikov hydrobromination of alkynes. Copper-catalyzed borylative cross-coupling of allenes and imines.

InChI:InChI=1/C27H36N2.ClH.Cu/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;;/h9-16,18-21H,1-8H3;1H;/q;;+1/p-1/rC27H36ClCuN2/c1-17(2)21-11-9-12-22(18(3)4)25(21)30-15-16-31(27(30)29-28)26-23(19(5)6)13-10-14-24(26)20(7)8/h9-20H,1-8H3

Upstream product

• 7647-01-0 hydrogenchloride 
• 250285-32-6 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride 
• 244187-81-3 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene 
• 258278-25-0 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride 
• 74663-75-5 1,2-bis(2,6-diisopropylphenylimino)ethane 
• 106-43-4 para-chlorotoluene 
• 12775-96-1 copper 
• 55718-76-8 2-chloro-1,3,2-benzodioxaborole 
• 73183-34-3 bis(pinacol)diborane 
• 81656-21-5 2-chloro-1,3,2-dioxa(BCH₂CMe₂CH₂) 
• 74663-75-5 (1E,2E)-N¹,N²-bis(2,6-diisopropylphenyl)-ethane-1,2-diimine 

Downstream Products

• 94647-81-1 2-tert-butoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1228216-70-3 C₂₇H₃₆ClN₂⁽¹⁺⁾ 

Relevant academic research and scientific papers

Cleavage of X-H bonds (X = N, O, or C) by copper(I) alkyl complexes to form monomeric two-coordinate copper(I) systems

The monomeric copper(I) alkyl complexes (IPr)Cu(R) [R = Me or Et; IPr= 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] react with substrates that possess N-H, O-H, and acidic C-H bonds to form monomeric systems of the type (IPr)Cu(X) (X = anilido, phenoxide, ethoxide, phenylacetylide, or N-pyrrolyl) and methane or ethane. Solid-state X-ray crystal structures of the anilido, ethoxide, and phenoxide complexes confirm that they are monomeric systems. Experimental studies on the reaction of (IPr)Cu(Me) and aniline to produce (IPr)Cu(NHPh) suggest that a likely reaction pathway is coordination of aniline to Cu(I) followed by proton transfer to produce methane and the copper(I) anilido complex.

Mechanochemical synthesis of Cu(i)-N-heterocyclic carbene complexes

We report a general, operationally simple and scalable mechanochemical method for the synthesis of [Cu(Cl)(NHC)] complexes. This solid-state and solvent-less methodology was shown to be applicable to a wide range of NHC ligand precursors, allowing access to complexes of the type [Cu(Cl)(NHC)] under aerobic conditions and with minimised environmental impact. This journal is

(NHC) CuI (NHC = N-Heterocyclic carbene) complexes as efficient catalysts for the reduction of carbonyl compounds

The hydrosilylation of various ketones is mediated by an imidazolium salt/Cu(I) salt system or by a well-defined (NHC)CuCl (NEC = N-heterocydic carbene) catalyst precursor system. Reactions are conducted at room temperature. The synthesis and characterization of well-defined (NHC)CuCl complexes are described.

Two-Coordinate Copper(I)/NHC Complexes: Dual Emission Properties and Ultralong Room-Temperature Phosphorescence

As a kind of photoluminescent material, CuI complexes have many advantages such as adjustable emission, variable structures, and low cost, attracting attention in many fields. In this work, two novel two-coordinate CuI-N-heterocyclic carbene complexes were synthesized, and they exhibit unique dual emission properties, fluorescence and phosphorescence. The crystal structure, packing mode, and photophysical properties under different conditions were systematically studied, proving the emissive mechanism to be the locally excited state of the carbazole group. Based on this mechanism, ultralong room-temperature phosphorescence (RTP) with a lifetime of 140 ms is achieved by selective deuteration of the carbazole group. These results deepen the understanding of the luminescence mechanism and design strategy for two-coordinate CuI complexes, and prove their potential in applications as ultralong RTP materials.

Simple and versatile selective synthesis of neutral and cationic copper(i) N-heterocyclic carbene complexes using an electrochemical procedure

An electrochemical approach for the preparation of copper(i) N-heterocyclic carbene complexes has been developed to include a diverse range of ligand precursors. Importantly, the method is effective for a ligand precursor that contains several acidic prot

N-Propargylation and Copper(I)-Catalyzed Azide-Alkyne Cycloaddition as a Convenient Strategy for Directed Post-Synthetic Modification of 4-Oxo-1,4-Dihydrocinnoline Derivatives

[Figure not available: see fulltext.] 4-Oxo-1,4-dihydrocinnoline derivatives as promising inhibitors of protein tyrosine phosphatase 1В were subjected to post-synthetic modification via a sequence of propargylation and copper(I)-catalyzed azide-alkyne cycloaddition reactions. The propargylation of 4-oxo- 1,4-dihydrocinnolines with propargyl bromide in the presence of various bases proceeded regioselectively at the cinnolinone N-1 atom. In the cycloaddition reaction of N-propargylcinnolinones and benzyl azide, the highest catalytic activity of copper(I) N-heterocyclic carbene complex [(IMes)Cu(Br,I)] was observed, compared to [(IMes)CuCl], [(IPr)Cu(Cl,Br,I)], and CuI.

Microwave-assisted synthesis of (N-heterocyclic carbene)MCl complexes of group 11 metals

The use of microwave heating for the synthesis of (N-heterocyclic carbene)-bearing complexes of Cu, Ag and Au allows for a drastic reduction of the reaction times required by conventional heating, while affording comparable or better yields of the desired complexes. Copyright

Unsymmetrical diborane(4) derivatives by copper mediated B-B coupling

A novel, versatile and modular route to unsymmetrical diborane(4) derivatives bearing either two different diol moieties or one diol and one diamine moiety is presented. Utilising the very basic approach of reacting a boron nucleophile with a boron electrophile to establish the B-B bond allows a simple variation of the two individual boron moieties. The copper(i) boryl complexes used as nucleophilic boron sources are readily accessible from commercially available symmetrical diborane(4) derivatives, whilst equally readily available boron halide derivatives are used as electrophiles. Seven previously inaccessible diborane(4) derivatives were obtained and fully characterised, including single crystal X-ray structure determinations, illustrating the broad scope of the method.

Addition of N-H and O-H bonds of amines and alcohols to electron-deficient olefins catalyzed by monomeric copper(I) systems: Reaction scope, mechanistic details, and comparison of catalyst efficiency

Monomeric copper(I) amido, alkoxide, and aryloxide complexes catalyze the addition of N-H and O-H bonds of amines and alcohols, respectively, to electron-deficient olefins. The ancillary ligands of the active catalysts include the N-heterocyclic carbene (

NHC copper(I) complexes bearing dipyridylamine ligands: Synthesis, structural, and photoluminescent studies

We describe the synthesis of new cationic tricoordinated copper complexes bearing bidentate pyridine-type ligands and N-heterocyclic carbene as ancillary ligands. These cationic copper complexes were fully characterized by NMR, electrochemistry, X-ray analysis, and photophysical studies in different environments. Density functional theory calculations were also undertaken to rationalize the assignment of the electronic structure and the photophysical properties. These tricoordinated cationic copper complexes possess a stabilizing CH-π interaction leading to high stability in both solid and liquid states. In addition, these copper complexes, bearing dipyridylamine ligands having a central nitrogen atom as potential anchoring point, exhibit very interesting luminescent properties that render them potential candidates for organic light-emitting diode applications.