An efficient 3-acylquinoline synthesis from acetophenones and anthranilviaC(sp³)–H bond activation mediated by Selectfluor

Abstract

An efficient method for the synthesis of 3-functionalized quinolines from acetophenones and anthranil mediated by Selectfluor was achieved.

Methylene-Tethered Arylsulfonation and Benzotriazolation of Aryl/Heteroaryl C–H Bonds with DMSO as a One-Carbon Surrogate

“…From this experiment, it can be concluded that the aryl sodium sulfinate ( 2a ) is more nucleophilic than benzotriazole ( 2ab ). Based on these mechanistic insights and previous literature, a plausible reaction mechanism is proposed (Figure B). Dimethyl sulfoxide (DMSO) is activated by Selectfluor to produce a methyl­(methylene)­sulfonium cation, which then reacts with imidazopyridine ( 1a ) to form a key intermediate 2aa , followed by nucleophilic displacement of SCH 3 with 2a or 2ab results in the formation of 3a or 4a .…”

Transition-metal-free C–S bond cleavage and transformation of organosulfur compounds

“…Finally, a spontaneous demethylthioation or demethylsulfinylation yields the intermediate 12E and MeSH or MeS(O)H (Scheme 13). 32…”

Recent Advances in the Application of Selectfluor as a “Fluorine‐free” Functional Reagent in Organic Synthesis

“…[28] Very recently, the same group reported a novel and efficent strategy for the construction of 3-acylquinoline by using acetophenone, anthranil and DMSO as the strating materials through a Selectuor mediated three-component reaction (Scheme 14c). [29] It was noteworthy to mention that DMSO served as both a carbon and solvent source.…”