Related Experiment Video
Updated: Apr 4, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Electropositive Sulfur Activation for the Regioselective Amino Functionalization of Alkynyl Sulfonium Salts
Cheng Peng1, Qiang Huang1, Jinglei Chen1
1Key Laboratory of Green and Precise Synthetic Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China.
Abstract:
We report an electropositive sulfur activation strategy for regioselective alkyne amination, enabling the tunable amino functionalization of alkynyl sulfonium salts with triazoles under ambient conditions. The operationally simple protocol exhibits a broad substrate scope and excellent functional-group tolerance, delivering vinyl triazoles in moderate to excellent yields. Both the control experiments and the isolation of key intermediates support a stepwise reaction pathway for this chemical process.
More Related Videos
Related Concept Videos
Preparation and Reactions of Sulfides
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

