Related Experiment Video
Updated: Jul 1, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Scandium-catalyzed chemoselective carbene insertion into N-H over S-H: access to o-alkylamine-diaryl disulfides
Haoyany Sun1, Junhong Pan1, Wenying Zhao1
1Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education; Yunnan Key Laboratory of Research & Development for Natural Products; School of Pharmacy, Yunnan University, Kunming, 650091, P.R. China. jinyi@ynu.edu.cn.
Abstract:
Herein, we report a scandium-catalyzed chemoselective carbene insertion into a N-H bond over a S-H bond with disulfide formation. This reaction represents the first example of the synthesis of o-alkylamine-diaryl disulfides through the N-alkylation of o-aminobenzenethiol, while also undergoing oxidative coupling to form a S-S bond. Control experiments explain the chemo-selectivity of this rare-earth-metal Lewis acid-induced catalysis by a carbene outer-sphere nucleophilic addition mechanism. This method holds tremendous potential as a valuable tool for functionalizing advanced-synthetic-intermediates, offering numerous applications in medicinal and materials chemistry.
More Related Videos
Related Concept Videos
Preparation and Reactions of Sulfides
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Radical Substitution: Allylic Bromination
SN2 Reaction: Transition State
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
Nucleophilic Aromatic Substitution: Elimination–Addition

