37438-01-0

Upstream product

• 142-29-0 cyclopentene 
• 108-88-3 toluene 
• 96-41-3 Cyclopentanol 
• 16156-57-3 cyclopentyl methanesulfonate 
• 95-46-5 2-methylphenyl bromide 
• 1239384-17-8 [2-(2-hydroxyprop-2-yl)phenyl]tricyclopentylsilane 
• 120-92-3 cyclopentanone 
• 932-31-0 ortho-tolylmagnesium bromide 
• 137-43-9 Cyclopentyl bromide 

Relevant academic research and scientific papers

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.

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.

Cross-coupling reactions through the intramolecular activation of Alkyl(triorgano)silanes

(Figure Presented) Cross-Si-ing the Jordan: Cross-coupling reactions of 2-(2-hydroxyprop-2-yl)phenylsubstituted alkylsilanes with a variety of aryl halides proceed in the presence of palladium and copper catalysts. The use of K3PO4 base allows for highly chemoselective alkyl coupling with both primary and secondary alkyl groups (Alk).

Detailed Characterization of p-Toluenesulfonic Acid Monohydrate as a Convenient, Recoverable, Safe, and Selective Catalyst for Alkylation of the Aromatic Nucleus

Alkylation of the aromatic nucleus, an important reaction in industry and synthetic organic chemistry, has traditionally been carried out by the well-known Friedel-Crafts reaction employing Lewis acid catalysts such as AlCl3 and BF3 or by using highly reactive organometallic reagents. Although protic acids such as anhydrous HF and concentrated H2SO4 have also been used in the alkylation of the aromatic nucleus, the notoriously corrosive, highly toxic, and hazardous nature of these agents has precluded their common use under ordinary laboratory conditions. Various organic sulfonic acids have, on occasion, been used as catalysts in Friedel-Crafts alkylations, but to our knowledge the chemistry and the scope of these reactions for common laboratory use have never been exploited in detail. In the present study we have characterized commercially available p-toluenesulfonic acid monohydrate (TsOH) as an efficient catalyst for the intermolecular coupling of the aromatic nucleus with activated alkyl halides, alkenes, or tosylates under mild conditions in an open atmosphere. In comparison to conventional Friedel-Crafts catalysts such as AlCl3, BF3, HF, and concentrated H2SO4, the extent of the formation of undesired products from side reactions such as transalkylation, polymerization, etc. was minimal with the TsOH-catalyzed reaction. The ability to recover and reuse the catalyst from the reaction mixtures, minimal generation of environmentally unfriendly waste, high specificity of the reaction, and the low cost of the catalyst are important advantages of the TsOH catalyst over the other conventional Friedel-Crafts catalysts.

Nuclear Heptylation of Benzene and Naphthalene and Cyclopentylation of Toluene

Thermal decomposition of 1-, 2-, 3- and 4-heptyltoluene-p-sulphonates in the presence of aromatic substrates like benzene or naphthalene at 130-35 deg, affords differently substituted α- and β-isomers in the case of naphthalene.Skeletal isomerisation of the alkyl group is observed where different isomeric 1-, 2-, 3- and 4-heptyl-aromatics are obtained.Also thermal decomposition of cyclopentylmethane sulphonate in the presence of toluene at 130-35 deg, furnishes the corresponding o-, m- and p-substituted toluenes.The isomers have been identified and estimated quantitatively by GLC.