93845-93-3

Upstream product

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 28141-32-4 2-Iodo-cyclohexanol 
• 67-64-1 acetone 
• 110-83-8 cyclohexene 
• 20668-24-0 4-Methylchinolin-2-d⁽¹⁾ 
• 143671-61-8 4-methylquinoline trifluoroacetate 

Downstream Products

• 106719-56-6 2-(cyclohexen-1′-yl)-4-methylquinoline 

Relevant academic research and scientific papers

Visible-light-mediated three-component Minisci reaction for heteroarylethyl alcohols synthesis

Methods for heteroarylethyl alcohol synthesis are critical to the chemical and pharmaceutical industries. Herein, we report a mild, modular, practical Minisci reaction for catalytic synthesis of heteroarylethyl alcohols via sequential addition of H2O and N-heteroarenes across olefinic double bonds. This scalable protocol was used for direct hydroxy-heteroarylation of olefins with a wide range of N-heteroarenes and can be expected to permit rapid conversion of abundant feedstock materials into medically relevant molecules.

Polar Effects in Free-Radical Reactions. Rate Constants in Phenylation and New Methods of Selective Alkylation of Heteroaromatic Bases

The rate constants for the addition of the phenyl radical to protonated and unprotonated 4-substituted pyridines have been determined by competition with chlorine abstraction from CCl4.The constants range from 2 * 105 to 6 * 106 M-1 s-1 depending on the substituent and on the degree of protonation.The phenyl radical shows a clear-cut nucleophilic character.On the basis of these rate constants, the use of phenyl radical from diazonium salt or benzoyl peroxide to generate alkyl radicals by iodine or hydrogen abstraction has been developed as a general procedure for the alkylation of heteroaromatic bases.This reaction is characterized by high yields and selectivities.

A NEW GENERAL METHOD OF HOMOLYTIC ALKYLATION OF PROTONATED HETEROAROMATIC BASES

Alkyl iodides and benzoyl peroxides provide a new general method of homolytic alkylation of protonated heteroaromatic bases.Yields are good and the substitution is selective in the positions ortho and para to the heteroatom.

Electron-transfer Processes: Metal Salt Catalysed Oxidation of Olefins by Peroxydisulphate

The reaction of simple olefins (oct-1-ene, oct-2-ene, cyclohexene, cycloheptene) with peroxydisulphate has been investigated under several conditions: (i) in aqueous medium and catalysis by AgI, FeII, and CuII; (ii) in acetic madium and catalysis by CuII, FeIII; (iii) in the presence of traps of nucleophilic alkyl radicals (protonated heteroaromatic bases and 1,4-benzoquinone either in water or in acetic acid).The catalyst and the radical trap govern the selectivity and allow a variety of new synthetic achievements.Evidence for a unified initial mechanism of electron transfer with formation of a radical cation from the olefin is reported to explain all the results.In water the radical cation gives a β-hydroxyalkyl radical, which, depending on the nature of the catalyst and the trap, can give the corresponding saturated alcohol by hydrogen abstraction, the products of CuII oxidation, or β-hydroxyalkylation of the heteroaromatic compound or 1,4-benzoquinone.In acetic acid the radical cation gives a β-acetoxyalkyl radical, which is oxidized to the corresponding allylic acetate by copper(II) acetate or trapped by the heteroaromatic base.

POLAR EFFECTS IN FREE-RADICAL REACTIONS. A NEW TYPE OF HOMOLYTIC AROMATIC ALKYLATION BY SILVER CATALYZED OXIDATION OF ACETONE BY PEROXYDISULPHATE IN THE PRESENCE OF OLEFINS.

Silver catalyzed peroxydisulphate oxidation of acetone in the presence of olefins and protonated heteroaromatic bases leads to compound I via addition of acetonyl radical to the olefin and scavenging of the resulting radical adduct by the aromatic base.