Four-component reaction strategy for β-alkylimide synthesis via organophotoredox catalysis
Camilo Verdugo1,2, Marco A Henriquez1,2, Prithwa Das2
1Departamento de Química Inorgánica, Escuela de Química, Facultad de Química y de Farmacia, Pontificia Universidad Católica de Chile, Vicuña Mackenna 4860, Macul, Santiago, 7820436, Chile. arcabrer@uc.cl.
Abstract:
We report a strategy for the four-component coupling of commercially available carboxylic acids, nitriles, N-(acyloxy)phthalimide esters (NHPI esters), and vinylarenes using 3DPAClIPN as an organophotocatalyst, affording 35 new β-alkylimides in 10-94% yield. Organic transformations on the alkylimide skeleton allow access to amides and amines in good yields.
More Related Videos
Related Concept Videos
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is activated by...
Alkynes 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.
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
α-Alkylation of Ketones via Enolate Ions


