Electrochemical Site-Specific Dehydrogenative Hydroxyalkylation of Purine Nucleosides with Alcohols
Qi-Liang Yang1, Shu-Xian Liu1, Ye Zhu1
1State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Abstract:
An electrochemical protocol for C6-selective hydroxyalkylation of purine nucleosides with alcohols via direct C(sp2)-C(sp3) cross-coupling was established. The protocol employed N-Hydroxyphthalimide (NHPI) as a hydrogen atom transfer mediator, yielding C6-hydroxyalkyl purine nucleosides in moderate to excellent yields. This electrochemical method is distinguished by its mild oxidant-free conditions, good regioselectivity, readily available raw materials, and validity for the late-stage modification of bioactive molecules. Mechanistic studies suggested that the reaction proceeded via an electro-generated α-hydroxyalkyl radical.
More Related Videos
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Base-Catalyzed Aldol Addition Reaction
α-Alkylation of Ketones via Enolate Ions
Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
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.
Hydroboration-Oxidation of Alkenes
