42470-80-4

Upstream product

• 106-47-8 4-chloro-aniline 
• 109-00-2 3-HYDROXYPYRIDINE 
• 2028-74-2 p-chlorobenzenediazonium chloride 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 1679-18-1 4-Chlorophenylboronic acid 
• 13365-63-4 (4-chlorophenyl)(furan-2-yl)methanone 
• 631-61-8 ammonium acetate 

Relevant academic research and scientific papers

Aryl Radical Selectivity in Biphasic Systems

Aryl radicals generated in the aqueous phase of biphasic mixtures have-regardless of a comparably low polarity- A strong preference to react with aromatic substrates in the aqueous phase and not to undergo phase-transfer into a lipophilic phase, independent from the presence of a surfactant. These results represent an important prerequisite toward future studies in biological systems, which typically consist of various compartments of either hydrophilic or lipophilic character.

Frozen aryldiazonium chlorides in radical reactions with alkenes and arenes

Frozen aryldiazonium chlorides have been investigated in radical alkene and arene functionalizations. Through freezing at – 84 °C, aryldiazonium chlorides, which otherwise show significant decomposition in aqueous solution after several hours at room temp

Visible-Light-Induced, Catalyst-Free Radical Arylations of Arenes and Heteroarenes with Aryldiazonium Salts

In the absence of a photocatalyst and other additives, the radical arylation of diverse arenes and heteroarenes has been achieved with aryldiazonium salts under visible-light irradiation from a blue light-emitting diode (LED). Although the course of some reactions can be rationalized by the formation of strongly light-absorbing charge-transfer (CT) complexes between the diazonium ion and the aromatic substrate, several further examples indicated that the simple presence of an aromatic substrate, showing only weak interactions to the diazonium ion, is fully sufficient to enable product formation.

Regioselective Radical Arylation of 3-Hydroxypyridines

The titanium(III)-mediated radical arylation of 3-hydroxypyridines was found to proceed with high regioselectivity for the 2-position. Using aryldiazonium chlorides, which were prepared from the corresponding anilines, as aryl radical sources, a range of 3-hydroxy-2-phenylpyridines were obtained in moderate to good yields under simple reaction conditions. Reactions of ortho-carboxylic ester substituted phenyldiazonium salts directly provided tricyclic benzopyranopyridinones.

Iridium-catalyzed selective hydrogenation of 3-hydroxypyridinium salts: A facile synthesis of piperidin-3-ones

The selective hydrogenation of 3-hydroxypyridinium salts has been achieved using a homogeneous iridium catalyst, providing a direct access to 2- and 4-substituted piperidin-3-one derivatives with high yields, which are important organic synthetic intermediates and the prevalent structural motifs in pharmaceutical agents. Mild reaction conditions, high chemoselectivity, and easy scalability make this reaction highly practical for the synthesis of piperidin-3-ones.