Selective Oxidative Methyl C-H Functionalization of Butylated Hydroxytoluene toward Arylimines/N-Heterocycles
Jianyu Dong1, Shaofeng Wu1,2, Furong Geng1,3
1School of Physics and Chemistry, Hunan First Normal University, Changsha 410205, China.
Abstract:
A metal-free and selective oxidative methyl C-H functionalization of BHT with aniline compounds has been developed. This innovative method enables the facile and efficient synthesis of a diverse array of BHT-functionalized N-containing skeletons, including arylamines, benzoxazoles, benzothiazoles, benzimidazoles, quinazolines, and quinazolinones, all of which are challenging to access. The control experiment involving TEMP18O suggests that the radical adduct of TEMPO with the benzyl radical of BHT may serve as an intermediate.
Related Concept Videos
03:08Hydroboration-Oxidation of Alkenes
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene