168554-86-7

Upstream product

• 38487-86-4 2-amino-4-chlorobenzonitrile 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 39061-72-8 2-acetyl-5-chloroaniline 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 823-57-4 2-bromo-5-chloroaniline 
• 5900-58-3 2-amino-4-chloro-benzoic acid methyl ester 
• 182740-45-0 2-(2-amino-4-chlorophenyl)-2-propanol 

Downstream Products

• 1009368-33-5 N-[5-chloro-2-(1-methylethenyl)phenyl]formamide 
• 2540-09-2 7-chloro-4-methyl-1,2-dihydroquinolin-2-one 
• 1346130-90-2 (S)-1-(7-chloro-4-methyl-2-phenylquinolin-1(2H)-yl)-2,2,2-trifluoroethanone 
• 1346130-64-0 (S)-5-chloro-N-(1-phenylallyl)-2-(prop-1-en-2-yl)aniline 

Relevant academic research and scientific papers

Convenient synthesis of fluorinated quinoline, 1,2-dihydroquinoline, and 1,2,3,4-tetrahydroquinoline derivatives

A convenient synthetic method for 2-polyfluoroalkylated quinoline systems through the efficient generation of perfluoroalkylated imine from o-vinylanilines with perfluorinated hemiacetals or aldehyde hydrates was developed. In most cases, the major produc

Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks

Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.

Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.

Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles

A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallography. With PISA, various indoles were synthesized via C-H amination of 2-alkenylanilines involving an aryl migration/intramolecular cyclization cascade with excellent regioselectivity in aqueous CH3CN. Notably, using this new method as the key step, not only two drug molecules, indometacin and zidometacin, but also another bioactive molecule, pravadoline, were synthesized.

Palladium-catalyzed direct coupling of 2-vinylanilines and isocyanides: An efficient synthesis of 2-aminoquinolines

Palladium-catalyzed oxidative coupling of 2-vinylanilines and isocyanides constitutes a direct, facile, and efficient approach to 2-aminoquinolines. The procedure, employing palladium acetate and silver carbonate, is attractive in terms of assembly efficiency, functional group tolerance, and operational simplicity. A variety of 2-aminoquinolines were prepared in good to excellent yields.

Copper-catalyzed trifluoromethylation of alkenes: Synthesis of trifluoromethylated benzoxazines

A simple base and ligand free copper catalyzed method for the construction of trifluoromethylated benzoxazines has been developed by using Umemoto's reagent. It involves the oxidative difunctionalization of alkenes through tandem C-O and C-CF3 bond formations. Furthermore, synthesized benzoxazines were selectively converted into trifluoromethylated allylic and (E)-vinylic benzamides by the treatment of KOtBu and CH3Li, respectively.