Skeletal editing of pyridines to aryldialdehydes
Meixin Yan1, Yonglin Shi1, Cong Lv1
1Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, PR China.
Abstract:
Electron-deficient nitrogen-containing aromatic heterocycles, particularly pyridine derivatives, can be converted into all-carbon aromatic frameworks via the ANRORC (Addition of Nucleophile, Ring-Opening, and Ring-Closing) skeletal editing process, providing a convenient tool for molecular diversification. However, reported methods are mainly limited to nucleophilic modification of ring-opening species. Herein, we report a distinct electrophilic modification method, smoothly converting pyridines into arene-1,3-dialdehydes or naphthalene-1,3-dialdehydes.
More Related Videos
Related Concept Videos
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Nucleophilic Aromatic Substitution: Elimination–Addition
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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry


