1453491-64-9

Upstream product

• 931002-48-1 3-(4-methoxyphenyl)-N-(quinolin-8-yl)propanamide 
• 66003-76-7 Diphenyliodonium triflate 
• 578-66-5 8-amino quinoline 
• 696-62-8 para-iodoanisole 
• 645-45-4 hydrocinnamic acid chloride 
• 867347-49-7 3-phenyl-N-(quinoline-8-yl)propionamide 
• 104-92-7 1-bromo-4-methoxy-benzene 

Relevant academic research and scientific papers

Multicomponent reaction comprising one-pot installation of bidentate directing group and Pd(II)-catalyzed direct β-arylation of C(sp3)[sbnd]H bond of aliphatic and alicyclic carboxamides

In this paper, we report a step-economical one-pot multicomponent reaction protocol comprising the installation of the bidentate directing group (auxiliary) followed by Pd(II)-catalyzed sp3C[sbnd]H activation and β-arylation of various aliphatic/alicyclic carboxamides. Accordingly, the reaction of a mixture of an aliphatic/alicyclic acid chloride, bidentate directing auxiliary (e.g., 8-aminoquinoline) and an aryl iodide in the presence of the Pd(OAc)2catalyst and Ag2CO3additive directly afforded the corresponding β-C[sbnd]H-arylated N-(quinolin-8-yl)carboxamide derivative. To demonstrate the efficiency of the process, various bidentate directing auxiliaries were used and 8-Aminoquinoline was found to be the best directing group for accomplishing the one-pot Pd(II)-catalyzed, sp3C[sbnd]H activation and β-arylation of aliphatic/alicyclic carboxamides. A variety of aliphatic/alicyclic acid chlorides and aryl iodides were used as the substrates and several β-C[sbnd]H arylated carboxamide derivatives were synthesized in moderate to high yields via the multicomponent reaction strategy.

Palladium-Catalyzed Asymmetric Arylation of C(sp3)-H Bonds of Aliphatic Amides: Controlling Enantioselectivity Using Chiral Phosphoric Amides/Acids

Enantioselective arylation of secondary β-C(sp3)-H bonds of 8-aminoquinoline amides was realized with a palladium catalyst. Chiral phosphoric amides and acids were used for the first time to control the stereoselectivity at the C-H bond cleavag

Pd(II)-catalyzed intermolecular arylation of unactivated C(sp 3)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary

An example of using readily available, less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp3)-H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K2CO3 base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp3)-H activation-led pathway featuring the oxidative addition as the highest energy transition state.

Direct arylation of primary and secondary sp3 C-H bonds with diarylhyperiodonium salts via Pd catalysis

Palladium-catalyzed primary and secondary sp3 C-H bond arylation is reported. The method using diarylhyperiodonium salts as arylation reagents shows good functional group tolerance and proceeds under mild reaction conditions. The KIE experiment