An Unexpected Construction of 2‐Arylquinolines from N‐Cinnamylanilines through sp³ CH Aerobic Oxidation Induced by a Catalytic Radical Cation Salt

Abstract

An unexpected reactiono fc innamylanilines wasa chieved through the radical cations altinduced aerobic oxidation of sp 3 C À Hb onds,p roviding as eries of 2-arylquinolines. Them echanistic study shows that the cinnamylaniline waso xidized to an imine,w hich was attacked by the aniline generated throughd ecomposition of the corresponding imine.A fter further intramolecular cyclization and aromatization, 2-arylquinolinesw ere obtained. This reaction providesanew method to construct 2-arylquinolines from readily accessible starting materials.

Synthesis of Polysubstituted Quinolines from α-2-Aminoaryl Alcohols Via Nickel-Catalyzed Dehydrogenative Coupling

“…After 16 h, purification by column chromatography using 2% ethyl acetate in hexanes yielded 4da (89 mg, 81%) as a pale-yellow oil: 1 8-Chloro-2-phenylquinoline (4ea). 42 GP 1 was followed using nickel catalyst 3 (4 mg, 2.0 mol %), (2-amino-3-chlorophenyl)methanol 1e (94 mg, 0.6 mmol), and acetophenone 2a (60 mg, 0.5 mmol). After 16 h, purification by column chromatography using 2% ethyl acetate in hexanes yielded 4ea (98 mg, 82%) as a viscous oil: 1 7-Fluoro-2-phenylquinoline (4fa).…”

Three-Component Synthesis of 2-Substituted Quinolines and Benzo[f]quinolines Using Tertiary Amines as the Vinyl Source

“…Purified directly by flash column chromatography (on silica gel, petroleum ether/EtOAc = 40:1) to give a white solid (48.8 mg, 76% yield) . mp 176–178 °C.…”

Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst

“…Compound 1s was obtained as a pale yellow solid (41 mg, 87%) after purification by column chromatography on silica using a mixture of ethyl acetate and hexanes (1:6) as an eluent. Spectroscopic data were matched with the reported values …”