41010-07-5

Upstream product

• 106-42-3 para-xylene 
• 107-13-1 acrylonitrile 
• 3333-13-9 p-allyltoluene 
• 6727-73-7 4-iodobutyronitrile 
• 106-38-7 para-bromotoluene 
• 104-87-0 4-methyl-benzaldehyde 
• 589-18-4 4-Methylbenzyl alcohol 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 75-05-8 acetonitrile 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 4521-22-6 4-(4-methylphenyl)butyric acid 
• 112023-32-2 bis-(4-p-tolyl-butyryl)-amine 

Relevant academic research and scientific papers

C(sp3)-H bond functionalization with styrenesviahydrogen-atom transfer to an aqueous hydroxyl radical under photocatalysis

The redox-neutral addition of α-C-H bonds of acetonitrile and acetone to styrenes was enabledviathe hydrogen-atom transfer from relatively acidic and water-miscible C(sp3)-H bonds to an aqueous hydroxyl radical generated cleanly and iteratively

Coupling Photocatalysis and Substitution Chemistry to Expand and Normalize Redox-Active Halides

Photocatalysis can generate radicals in a controlled fashion and has become an important synthetic strategy. However, limitations due to the reducibility of alkyl halides prevent their broader implementation. Herein we explore the use of nucleophiles that can substitute the halide and serve as an electron capture motif that normalize the variable redox potentials across substrates. When used with photocatalysis, bench-stable, commercially available collidinium salts prove to be excellent radical precursors with a broad scope.

Low-Valent Titanium-Mediated Radical Conjugate Addition Using Benzyl Alcohols as Benzyl Radical Sources

A concise method to directly generate benzyl radicals from benzyl alcohol derivatives has been developed. The simple and inexpensive combination of TiCl4(collidine) (collidine = 2,4,6-collidine) and manganese powder afforded a low-valent titanium reagent, which facilitated homolytic cleavage of benzylic C-OH bonds. The application to radical conjugate addition reactions demonstrated the broad scope of this method. The reaction of various benzyl alcohol derivatives with electron-deficient alkenes furnished the corresponding radical adducts.

Visible-Light-Mediated Remote γ-C(sp3)-H Functionalization of Alkylimidates: Synthesis of 4-Iodo-3,4-dihydropyrrole Derivatives

An efficient and environmentally friendly synthetic approach toward functionalized dihydropyrrole derivatives is reported. The developed protocol proceeds via chemoselective intramolecular N-C bond formation of alkylimidates through 1,5-hydrogen atom transfer from in situ generated imidate N-radicals. The major advantage of this designed strategy lies in the choice of starting materials, mild reaction conditions, high chemo- and diastereoselectivity, clean source of energy, and good functional group tolerance. Further, 4-iododihydropyrroles could be easily transformed into a variety of useful derivatives.

CYANOETHYLATION OF HYDROCARBONS, INITIATED BY AUTOOXIDATION

Oxygen was used as an initiator of the free-radical cyanoethylation of alkylbenzenes (toluene, o-, m-, and p-xylenes, mesitylene, ethylbenzene, p-cymene) and tetralin (0.25-0.66 liter of oxygen to 1 liter of the hydrocarbon) The reactions were carried out in an autoclave at 150-350 deg C with a carbon-acrylonitrile ratio of 100:1.The initiation evidently results mainly from homolytic dissociation of the hydroperoxide formed during the autooxidation of the hydrocarbons.The effectiveness of oxygen for the initiation of the cyanoethylation of hydrocarbons depends on the oxidizability of the hydrocarbons.