827-55-4

Usage

Uses

Used in Pharmaceutical Synthesis:
Benzene, 1-cyclopentyl-4-methylis utilized as an intermediate in the production of various pharmaceuticals. Its unique structure allows for the creation of complex organic molecules that can be used in the development of new drugs, contributing to advancements in medicine.
Used in Agrochemical Production:
In the agrochemical industry, Benzene, 1-cyclopentyl-4-methylserves as a key intermediate in the synthesis of various agrochemicals. Its role in the production of pesticides and other agricultural chemicals helps to improve crop protection and yield.
Used as an Industrial Solvent:
Benzene, 1-cyclopentyl-4-methylis employed as a solvent in a range of industrial processes. Its solubility properties make it suitable for dissolving a variety of substances, facilitating chemical reactions and material processing in different sectors.

Upstream product

• 137-43-9 Cyclopentyl bromide 
• 106-38-7 para-bromotoluene 
• 142-29-0 cyclopentene 
• 108-88-3 toluene 
• 96-41-3 Cyclopentanol 
• 16156-57-3 cyclopentyl methanesulfonate 
• 106-43-4 para-chlorotoluene 
• 63076-51-7 cyclopentane boronic acid 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 930-28-9 cyclopentyl chloride 
• 827-56-5 1-(4-tolyl)cyclopentene 
• 120-92-3 cyclopentanone 

Downstream Products

• 22460-07-7 (±)-2-(p-tolyl)cyclopentan-1-one 
• 19936-22-2 p-cyclopentylbenzoic acid 
• 100256-66-4 p-Tolylcyclopentylhydroperoxid 

Relevant academic research and scientific papers

Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling

Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.

Pd-Catalyzed reductive heck reaction of olefins with aryl bromides for Csp2-Csp3 bond formation

We developed a Pd-catalyzed intermolecular reductive Heck reaction to construct Csp2-Csp3 bonds between aryl bromides and olefins. Various styrene derivatives, acyclic and cyclic alkenes, were well tolerated to couple with varied aryl bromides in linear selectivity. Kinetic and deuterium labeling experiments suggested that i-PrOH provides a hydride through β-H elimination.

Water Soluble Benzimidazole Containing Ionic Palladium(II) Complex for Rapid Microwave-Assisted Suzuki Reaction of Aryl Chlorides

In this paper a water soluble benzimidazole – Pd complex used for Suzuki reaction under conventional heating and microwave heating. To increase the activity of complex, ionic group change with bulky TBA+ and Bmim+ groups. To determine whether the reaction is homogeneous or heterogeneous, Hg(0) poisoning tests, hot filtration tests and CS2 poisoning tests were performed.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Alkyl Bromides: Et3N as the Terminal Reductant

Reductive cross-coupling has emerged as a direct method for the construction of carbon-carbon bonds. Most cobalt-, nickel-, and palladium-catalyzed reductive cross-coupling reactions to date are limited to stoichiometric Mn(0) or Zn(0) as the reductant. One nickel-catalyzed cross-coupling paradigm using Et3N as the terminal reductant is reported. By using this photoredox catalysis and nickel catalysis approach, a direct Csp2-Csp3 reductive cross-coupling of aryl bromides with alkyl bromides is achieved under mild conditions without stoichiometric metal reductants.

Iron phosphine catalyzed cross-coupling of tetraorganoborates and related group 13 nucleophiles with alkyl halides

Iron phosphine complexes prove to be good precatalysts for the cross-coupling of alkyl, benzyl, and allyl halides with not only aryl triorganoborate salts but also related aluminum-, gallium-, indium-, and thallium-based nucleophiles. Mechanistic studies revealed that while Fe(I) can be accessed on catalytically relevant time scales, lower average oxidation states are not formed fast enough to be relevant to catalysis. EPR spectroscopic studies reveal the presence of bis(diphosphine)iron(I) complexes in representative catalytic reactions and related processes with a range of group 13 nucleophiles. Isolated examples were studied by M?ssbauer spectroscopy and single-crystal X-ray structural analysis, while the electronic structure was probed by dispersion-corrected B3LYP DFT calculations. An EPR study on an iron system with a bulky diphosphine ligand revealed the presence of an S = 1/2 species consistent with the formation of a mono(diphosphine)iron(I) species with inequivalent phosphine donor environments. DFT analysis of model complexes allowed us to rule out a T-shaped Fe(I) structure, as this is predicted to be high spin.

Efficient cross-coupling of aryl Grignard reagents with alkyl halides by recyclable ionic iron(iii) complexes bearing a bis(phenol)-functionalized benzimidazolium cation

A novel bis(phenol)-functionalized benzimidazolium salt, 1,3-bis(3,5-di-tert-butyl-2-hydroxybenzyl)benzimidazolium chloride (H 3LCl, 1), was designed and used to prepare ionic iron(iii) complexes of the type [H3L][FeX4] (X = Cl, 2; X = Br, 3). Both 2 and 3 were characterized by elemental analysis, Raman spectroscopy, electrospray ionization mass spectrometry and X-ray crystallography. The catalytic performances of 2 and 3 in cross-coupling reactions using aryl Grignard reagents with primary and secondary alkyl halides bearing β-hydrogens were studied. This analysis shows that complex 2 has good potential for alkyl chloride-mediated coupling. In comparison, complex 3 showed slightly lower catalytic activity. After decanting the product contained in the ethereal layer, complex 2 could be recycled at least eight times without significant loss of catalytic activity.

Mild negishi cross-coupling reactions catalyzed by acenaphthoimidazolylidene palladium complexes at low catalyst loadings

Considering that the strong σ-donor property of ylidenes derived from π-extended imidazolium salts is conducive to increasing the catalytic activity of the resulting palladium N-heterocyclic carbene complexes, robust acenaphthoimidazol-ylidene palladium complexes 3a-c with varying bulky substituted groups were prepared from the corresponding acenaphthoimidazolium chlorides by heating with PdCl2 and K2CO3 in neat 3-chloropyridine in satisfactory yields. Even at a catalyst loading as low as 0.25 mol %, complex 3a exhibited extremely high catalytic activity toward Negishi cross-coupling of alkylzinc reagents with a wide range of (hetero)aryl halides under mild reaction conditions within 30 min. Besides a great number of bromoarenes, various less expensive and inactive (hetero)aryl chlorides were coupled successfully with the alkyl- and arylzinc reagents, in which active functional groups (such as -NH2) were well tolerated even in one-pot dicoupling transformations without protection. In addition, in the case of coupling with secondary alkylzinc reagents, undesired β-hydride elimination leading to isomerized linear products was efficaciously suppressed. The catalyst system also displayed superiority in the construction of heterobiaryls through the coupling of heteroarylzinc reagents and heterocylic chloroarenes which were hardly accessible from the corresponding organoboron reagents by Suzuki-coupling reactions. Therefore, the protocol described in this paper represents a mild, general, and scalable approach to access various structurally intriguing and functionalized (hetero)aryls.

Ionic iron(iii) complexes of bis(phenol)-functionalized imidazolium cations: Synthesis, structures and catalysis for aryl Grignard cross-coupling of alkyl halides

A series of bis(phenol)-functionalized imidazolium salts, 1,3-bis(4,6-di-R1-2-hydroxybenzyl)-2-R2-4,5-di-R 3-imidazolium chlorides H3LnCl (R1 = tBu, R2 = R3 = H, H3L 1Cl, 1; R1 = CH3, R2 = R3 = H, H3L2Cl, 2; R1 = tBu, R 2 = H, R3 = Cl, H3L3Cl, 3; R 1 = tBu, R2 = CH3, R3 = H, H3L4Cl, 4), were used to produce a novel series of ionic iron(iii) complexes [H3Ln][FeX4] (n = 1, X = Cl, 5; n = 2, X = Cl, 6; n = 3, X = Cl, 7; n = 4, X = Cl, 8; n = 1, X = Br, 9; n = 3, X = Br, 10). All of the complexes were characterized by Raman spectroscopy and electrospray ionization mass spectrometry. Elemental analysis and X-ray crystallography were also used. All of the complexes were non-hygroscopic and air-stable, with five of them existing as solids (5, 7-10) and one as an oil (6) at room temperature. A preliminary catalytic study on the cross-coupling reactions of aryl Grignard reagents with primary and secondary alkyl halides bearing β-hydrogens, revealed that all of the ionic iron(iii) complexes exhibited good to excellent catalytic activity. Complexes 5, 6 and 8 exhibited optimal activity, whereas 7, 9 and 10 showed only moderate activity. Furthermore, by simply decanting the cross-coupling product in the ether layer, complexes 5 and 6 could be reused in at least seven successive runs without significant loss in catalytic activity.

Highly effective activation of aryl chlorides for Suzuki coupling in aqueous media using a ferrocene-based Pd(II)-diimine catalyst

The Suzuki coupling of aryl chlorides with boronic acids using a ferrocene-containing Pd(II)-diimine complex as catalyst, in aqueous media, under microwave heating is reported. A small amount of the catalyst (0.1%) was found to be highly effective for coupling unactivated aryl chlorides with boronic acids to form sterically hindered ortho-substituted biaryls. The same catalyst also enabled the coupling of aryl bromides and iodides with various boronic acids in very high yields. The catalyst is air stable and the catalytic reaction can be completed in 15 min.

Iron(II) complexes with functionalized amine-pyrazolyl tripodal ligands in the cross-coupling of aryl Grignard with alkyl halides

Structurally distinctive Fe(ii) complexes with furan, thiophene and pyridine functionalized amine-pyrazolyl tripodal hybrid ligands have been synthesized and crystallographically characterized. The tether substituent at the central amine plays an active role in determining the coordination mode of the ligand and the metal geometry. All complexes are catalytically active towards cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides with β-hydrogen under ambient conditions. ESI-MS spectra analysis revealed the ligand-stabilised Fe(ii) and Mg(ii) species. The Royal Society of Chemistry 2011.