1595-10-4

Upstream product

• 543-59-9 1-Chloropentane 
• 95-47-6 o-xylene 
• 592-41-6 1-hexene 
• 108-88-3 toluene 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 623-55-2 (+-)-5-methyl-3-hexanol 
• 71-43-2 benzene 
• 627-59-8 5-methylhexan-2-ol 
• 2313-65-7 3-methyl-2-hexanol 
• 615-37-2 ortho-methylphenyl iodide 
• 542-69-8 1-iodo-butane 
• 1134-92-5 o-tolyl N,N-dimethylsulfamate 
• 44767-62-6 n-hexylmagnesium chloride 

Relevant academic research and scientific papers

Nickel metallodendrimers as catalyst precursors in the tandem oligomerization of ethylene and Friedel-Crafts alkylation of its olefinic products Metallodendrimers Special Issue

The synthesis and catalytic activity of nickel metallodendrimers (C1-C6) are reported. The metallodendrimers were synthesized by the coordination of the metal precursors, Ni(OAc)2 and Ni(DME)Br2, to the periphery of salicylaldimine and iminopyridyl modified dendritic ligands, DL1-DL6, based on the generation 1 to generation 3 diaminobutane polypropylene imine (DAB-PPI) dendrimers. The metallodendrimers were tested in the oligomerization of ethylene and were found to be active catalysts. When using this catalyst system, it was found that a tandem process occurred in which ethylene oligomerization was followed by Friedel-Crafts alkylation of the reaction solvent, toluene. The latter process is mediated by the aluminium co-catalyst, EtAlCl2.

Alkylation-Terminated Catellani Reactions Using Alkyl Carbagermatranes

The Catellani reaction has received substantial attention because it enables rapid multiple derivatization on aromatics. While using alkyl electrophiles to achieve ortho-alkylation was one of the earliest applications of the Catellani reaction, ipso-alkyl

Iron-catalyzed alkylations of aryl sulfamates and carbamates

The alkylation of aryl sulfamates and carbamates using iron catalysis is reported. The method constructs sp2-sp3 carbon-carbon bonds and provides synthetically useful yields across a range of substrates (>35 examples). The directing group ability of sulfamates and carbamates, accompanied by their low reactivity toward conventional cross-couplings, renders these substrates useful for the synthesis of polyfunctionalized arenes.

Ferrocenyl iminophosphine ligands in Pd-catalysed Suzuki couplings

A mixture of Pd2(dba)3/{η-C5H 4CHN[CH(CH3)(Nap)]}Fe[η-C5H 4P(tBu)2] efficiently catalyzes the Suzuki reactions of a variety of bulky aryl halides and aryl- and alkyl-boronic acids, affording the desired cross-coupling biaryl products in quantitative isolated yields under mild conditions and at low (1 × 10-6-1 mol%) Pd loadings. Spectroscopic (NMR & ESI) analysis of the mixture of Pd 2(dba)3, the hybrid [P,N] ligands, and aryl halides revealed different structural forms of oxidative addition products that are dependent on the substituent on the imino nitrogen.

Copper-catalyzed cross-coupling reaction of organoboron compounds with primary alkyl halides and pseudohalides

Non-activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper-catalyzed cross-coupling with aryl boron compounds and alkyl 9-BBN reagents (see scheme; 9-BBN=9-borabicyclo[3.3.1]nonane). The reactions proceed with practically useful reactivities and thus complement palladium- and nickel-catalyzed Suzuki-Miyaura coupling reactions of alkyl halides.

Syntheses, structures, and catalytic ethylene oligomerization behaviors of Bis(phosphanyl)aminenickel(II) Complexes containing N-functionalized pendant groups

Several N-functionalized bis(phosphanyl)amine ligands respectively containing benzyl, furfuryl, thiophene-2-methyl, thiophene-2-ethyl, and 2-picolyl groups (la-e) were synthesized and characterized. The ligands reacted with (DME)NiBr2 in CH2Cl2 to give their corresponding nickel complexes [Ph2PN(R)PPh2NiBr 2] [R = CH2C6H5 (2a), CH 2C4H3O (2b), CH2C4H 3S (2c), CH2C5H4N (2d), and CH 2CH2C4H3S (2e)], The structures of these complexes were established by single-crystal X-ray crystallography, All these nickel complexes were highly active towards ethylene oligomerization in the presence of methylaluminoxane or Et2AlCl, producing a high content of butene (C4), Especially for 2e, which contains a thiophene-2-ethyl pendant group, the oligomerization products obtained at -40 °C contained 95.9 mol-% C4 fraction with 100 mol-% 1-butene. Over 50 °C, however, these nickel complexes underwent: Friedel-Crafts alkylation of toluene with ethylene and the olefin oligomers.

Regioselective arene functionalization: Simple substitution of carboxylate by alkyl groups

Arenes with various alkyl side-chains were synthesized in high yields and excellent regioselectivities. Starting from toluic and naphthoic acids, the carboxylate group was conveniently substituted by alkyl halides by Birch reduction and subsequent decarbonylation. The method is characterized by inexpensive starting materials and reagents, and methylation of arenes was realized. Besides simple alkyl substituents, the scope of arene functionalization was extended by benzyl, fluoro, amino, and ester groups. We were able to control the alkylation of 1-naphthoic acid during Birch reduction by the addition of tert-butanol. This allowed the regioselective synthesis of mono and bis-substituted naphthalenes from the same starting material.

First Kumada reaction of alkyl chlorides using N-heterocyclic carbene/palladium catalyst systems

For the first time it is shown that N-heterocyclic carbenes are suitable ligands for the palladium-catalyzed coupling of alkyl chlorides with aryl Grignard reagents. A variety of simple as well as functionalized primary alkyl chlorides provide the corresponding alkyl benzenes in general in good to very good yield. By comparing the 1,3-dimesitylimidazol-2-ylidene (IMes) palladium(0) naphthoquinone complex with the previously known palladium phosphine catalyst for the model coupling reaction of 1-chlorohexane with phenylmagnesium bromide it is demonstrated that the new catalyst system is superior.

Palladium-catalyzed coupling of alkyl chlorides and Grignard reagents

Chloroalkanes refined: A simple catalyst system renders the palladium-catalyzed coupling reaction of functionalized alkyl chlorides and Grignard reagents at room temperature (see example in scheme; PCy3 = tricyclohexylphosphane, NMP = N-methylpyrrolidinone).