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Usage

Uses

Used in Pharmaceutical Industry:
Iodtris(triphenylphosphino)kupfer is used as a catalyst for the efficient and selective synthesis of complex organic molecules, which are crucial in the development of new pharmaceutical compounds. Its ability to promote coupling reactions, such as the Ullmann coupling, aids in the creation of diverse molecular structures that can be utilized in drug discovery and medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, Iodtris(triphenylphosphino)kupfer serves as a catalyst for the synthesis of complex organic molecules used in the development of agrochemicals, including pesticides and herbicides. Its catalytic properties enable the production of these compounds with high selectivity and efficiency, contributing to the advancement of agricultural technologies.
Used in Organic Synthesis:
Iodtris(triphenylphosphino)kupfer is utilized as a catalyst in various organic synthesis reactions, particularly for the formation of carbon-carbon bonds. Its role in promoting coupling reactions, such as the Ullmann coupling, is essential for the synthesis of a wide range of organic compounds, including those with potential applications in materials science, chemical research, and the development of new chemical entities.

Upstream product

• 7681-65-4 copper(l) iodide 
• 603-35-0 triphenylphosphine 
• 190141-84-5 trans-Pd(I)(C₆H₄Me-p)(PEt₃)2 

Downstream Products

• 959904-63-3 [Cu(triphenylphosphine)2(piperidin-N-yl-C(S)NP(S)(O-i-Pr)2)] 
• 664980-32-9 [Cu(PPh₃)2(N-(diisopropoxythiophosphinyl)-N'-phenylthiourea(-1H))] 
• 959904-64-4 [Cu(triphenylphosphine)2(PhCH₂NHC(S)NP(S)(O-i-Pr)2)] 
• 959904-62-2 [Cu(triphenylphosphine)2(morpholin-N-yl-C(S)NP(S)(O-i-Pr)2)] 
• 928759-30-2 [Cu(triphenylphosphine)2(H₂NC(S)NP(S)(O-i-Pr)2)] 
• 166662-81-3 [(P(C₆H₅)3)2Cu(C₅H₈N₂)I] 
• 505058-74-2 [CuI(N-carboethoxy-4-bromobenzene thioamide)(PPh₃)2] 
• 166662-80-2 [(P(C₆H₅)3)2Cu(C₃H₄N₂)I] 
• 182013-62-3 [(triphenylphosphine)(4-phenylimidazolate)2Cu] 
• 144749-79-1 {Cu(P(C₆H₅)3)2(C₆H₅NHC(S)N((CH₂)3CH₃)2)I} 
• 144749-76-8 {Cu(P(C₆H₅)3)2(C₆H₅NHC(S)N(CH₃)2)I} 
• 144749-81-5 {Cu(P(C₆H₅)3)2(C₃H₅NS₂)I} 
• 144886-69-1 {Cu(P(C₆H₅)3)2(C₆H₅NHC(S)N(CH₂CH₂)2O)I} 
• 144886-63-5 {Cu(P(C₆H₅)3)2(C₆H₅NC(O)CH₂NHC(S))I} 

Relevant academic research and scientific papers

Polymorph and isomer conversion of complexes based on CuI and PPh 3 easily observed via luminescence

Reactions between copper(i) iodide and triphenylphosphine have been explored in solution and in the solid state and six luminescent coordination complexes have been obtained and characterized by X-ray diffraction and UV-vis spectroscopy and photophysics.

Heteroleptic copper(i) halides with triphenylphosphine and acetylthiourea: Synthesis, characterization and biological studies (experimental and molecular docking)

Nine new copper complexes with the general formula [CuX(TPP)n(ATU)3-n] (where X = Cl, Br, and I, ATU = acetylthiourea, TPP = triphenylphosphine and n varies as 0, 1 and 2) were synthesized in a simple fashion, by changing the ratio of the ligands. The synthesized complexes were characterized by techniques, such as FT-IR and NMR spectroscopy, CHNS elemental analysis and single crystal X-ray technique. The XRD technique showed the monodentate behavior of TPP and ATU. The synthesized compounds were utilized in different biological assays, which showed anti-bacterial, anti-fungal, anti-lieshmanial, anti-oxidant and cytotoxic properties against brine shrimps. In parallel, molecular docking was carried out to decipher the binding conformation and chemical interactions of the compounds in the active binding pockets of biological drug targets against bacterial pathogens and lieshmanial parasite, as well as a cancer target. All these analyses revealed compounds [CuCl(TPP)(ATU)2] and [CuI(TPP)(ATU)2] to be the most effective molecules of the series. Molecular docking indicated that hydrogen bonding and hydrophobic pi-interactions play important role for the activities of complexes with ligands TPP/ATU ratio of 1/2.

Copper(I)-catalyzed stereoselective synthesis of (1E,3E)-2- sulfonyl-1,3-dienes from N-propargylic sulfonohydrazones

A new method for the stereoselective synthesis of highly substituted (1E,3E)-2-sulfonyl-1,3-dienes from N-propargylic sulfonohydrazone derivatives has been developed via copper(I)-catalyzed [3,3] rearrangement and highly regioselective migration of the sulfonyl group. Copyright

Synthesis and structures of 3-sila-β-diketiminato complexes of the coinage metals

The dimeric copper(I) 3-sila-β-diketiminate [Cu{(N(R)C(Ar))2SiR}]2 · (thf) (1) was obtained from CuI and [Li{(N(R)C(Ar))2SiR}(thf)2] (B) in toluene (R = SiMe3, Ar = C6H3Me2-2,6). When [CuI(PPh3)3] was used as a starting material, the LiI-containing compound [Cu{Si(R)(C(Ar)N(R))2Li(μ-I)}(PPh3)] (2) was isolated. The reaction of [MI(PPh3)n] (M = Ag, n = 3; M = Au, n = 2) with two equivalents of B in toluene gave the isomorphous silver and gold 3-sila-β-diketiminates [M{Si(R)(C(Ar)N(R))2Li}2(μ-I)] [M = Ag (3), Au (4)]. Each of 1-4 was characterised by the multinuclear NMR spectroscopy and single-crystal X-ray diffraction crystallography.

Structural and solid state31P NMR studies of the four-coordinate copper(I) complexes [Cu(PPh3)3X] and [Cu(PPh 3)3(CH3CN)]X

The tris(triphenylphosphine)copper(I) complexes [(PPh3) 3CuX] for X = Cl (1), Br (2), I (3), ClO4 (4), BF 4 (5), [(PPh3)3CuCl]·CH3CN (1a), [Cu(PPh3)3(CH3CN)]X for X = ClO 4 (6), BF4 (7), and [Cu(PPh3) 3(CH3CN)]X·CH3CN for X = SiF5 (8), PF6 (9) have been studied by solid state 31P CP/MAS NMR spectroscopy together with single crystal X-ray diffraction for compounds (6)-(9), the latter completing the availability of crystal structure data for the series. Compounds (1)-(5) form an isomorphous series in space group P3 (a ～ 19, c ～ 11 A) with three independent molecules in the unit cell, all disposed about 3-fold symmetry axes. Average values (with estimated standard deviations) for the P-Cu-P, P-Cu-X bond angles and Cu-P bond lengths in compounds (1)-(3) are 110.1(6)°, 108.8(6)° and 2.354(8) A and 115.2(6)°, 102.8(9)° and 2.306(9) A for compounds (4) and (5). For the acetonitrile solvated compound (1a), the corresponding parameters are 115(4)°,103(3)° and 2.309(3) A. The solid state 31P CP/MAS NMR quadrupole distortion parameters, dvCu, for (1)-(3) and (1a) are all less than 1 × 109 Hz2, despite the changes in donor properties of the halide in (1)-(3), and the coordination geometry of the P3CuX core in (1a). Change of anion to ClO 4- and BF4- in compounds (4) and (5) results in a significant increase of dvCu to 4.4-5.2 109 Hz2 and 5.2-6.0 × 109 Hz2, respectively. Compounds (6) and (7) crystallise as isomorphous [Cu(PPh3) 3(CH3CN)]X salts in space group Pbca, (a ～ 17.6, b ～22.3, c ～24.2 A), while compounds (8) and (9) crystallize as isomorphous acetonitrile solvated salts [Cu(PPh3)3(CH 3CN)]X·CH3CN in space group P1 (a ～ 10.5, b ～ 13.0, c ～19.5 A, a ～ 104, β ～ 104, γ ～ 94°). The P3CuN angular geometries in all four compounds are distorted from tetrahedral symmetry with average P-Cu-P, P-Cu-N angles and Cu-P bond lengths of 115(4)°, 103(4)° and 2.32(1) A, with dv Cu ranging between 1.3 and 2.5 × 109 Hz2. The solid state 29Si CP/MAS NMR spectrum of the pentafluorosilicate anion in compound (8) is also reported, affording 1J(29Si, 19F) = 146 Hz. The Royal Society of Chemistry 2005.

Preparation and properties of trans-Pd(Ar) (C≡CPh) (PEt3)2. Intermolecular alkynyl ligand transfer between copper(I) and palladium(II) complexes relevant to palladium complex catalyzed cross-coupling of terminal alkyne with haloarene in the presence of CuI cocatalyst

trans-Pd(C6H4Me-p)(I)(PEt3)2 (2a) reacts with [Cu(C≡CPh)(PPh3)]4 (Pd:Cu = 1:1) at room temperature to give the cross-coupling product PhC≡CC6H4Me-P (3a) in 74% yield. Reactions of 2a with [Cu(C≡CPh)(PPh3)I4 at -30 °C as well as of trans-Pd(C6H4X-P)(I)(PEt3)2 (2a, X = Me; 2b, X = OMe; 2c, X = F) with the alkynylcopper complex and additional PPh3 (2 mol/ mol of Cu) at room temperature give mixtures of PhC≡CC6H4X-P (3a, X = Me; 3b, X = OMe; 3c, X = F) and trans-Pd(C6H4X-P)(C≡CPh)(PEt3) 2 (4a, X = Me; 4b, X = OMe; 4c, X = F). Complexes 4a,b have been isolated from the latter reaction mixtures and fully characterized. Pd-C(alkynyl) and Pd-C(aryl) bond distances in 4a are 2.016(8) and 2.062(7) A, respectively. Addition of Cul to a solution of 4a at room temperature causes complete conversion of 4a into 2a and 3a in 1 h. The relative molar ratio between 2a and 4a after reaction for 2 h varies, depending on the amount of added PPh3. Reactions of trans-Pt(C6H4X-p)(I)(PEt3)2 (5b, X = OMe; 5c, X = F) with [Cu(C≡CPh)(PPh3)]4 at room temperature afford trans-Pt(C6H4X-p)(C≡CPh)(PEt3) 2 (6b, X = OMe; 6c, X = F), respectively. Heating an equimolar mixture of 4a and 5b at 35-50 °C leads to inter-metal exchange of the alkynyl and iodo ligands, giving 2a and 6b quantitatively. The reaction follows the kinetics that is first order in concentration of 4a and in that of 5b. The kinetic parameters are obtained as ΔH? = 110 kJ mol-1, ΔS? = -58 J mol-1 deg-1, and ΔG? = 127 kJ mol-1 at 298 K. The alkynyl ligand migration from Pd(II) to Pt(II) is enhanced by addition of a catalytic amount of CuI.

Solution equilibria of tertiary phosphine complexes of copper(I) halides

The solution equilibria in benzene of arylphosphine complexes of the type LmCunXn (L = Ph3P, MePh2P; X = Cl, Br, I; m:n = 3:1, 4:2, 3:2, 2:2, 4:4) have been investigated by using UV spectrometry and vapor pressure osmometry. The halogen appears to have only a minor effect on the dissociation. A detailed analysis of the chloride complexes shows that ligand dissociation of the L3CuCl complexes is also accompanied by dimerization of the coordinately unsaturated copper(I) complexes through halogen bridging. However, the dimeric and tetrameric species formed by halogen bridging are found to be significant species in solution only when the ratio of L to CuCl is less than 3:1. An equilibria system is proposed with equilibrium constants derived from the modeling of the experimental data. The constants for the single ligand dissociation from (Ph3P)3CuCl and (MePh2P)3CuCl are 2 × 10-2 and 2 × 10-4, respectively. With the much greater dissociation of the Ph3P complex, the (Ph3P)2CuCl species is the dominant form in a benzene solution made from the solid-state (Ph3P)3CuCl complex. Solution profiles of different ratios of L to CuCl are generated to show how various species present in solution vary with concentration. The stability of the LmCunCln complexes (Ph3P ? MePh2P) toward ligand dissociation is attributed to greater steric interactions of Ph3P in comparison to MePh2P.