Related Experiment Video
Updated: May 21, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Silver-Catalyzed Halochalcogenation of Terminal Alkynols to Access Halogenated Selenonaphthalenes
Huanliang Hong1, Li Wang1, Sijie Xie1
1School of Environmental and Chemical Engineering, Wuyi University, Jiangmen, Guangdong Province, 529090, China.
Abstract:
Herein, we report an AgNO3 and FeCl3 relay-catalyzed halogenation and electrophilic selenium cyclization reaction. This reaction is based on the trifunctionalization of terminal alkynols using NBS and diorganyl diselenides, providing a step-efficient synthetic approach to produce halogenated selenonaphthalene derivatives in good yields. Furthermore, the halochalcogenation and cyclization reaction offers an efficient protocol for constructing molecules with two independent reactive centers.
More Related Videos
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Related Concept Videos
Electrophilic Addition to Alkynes: Hydrohalogenation
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the Ï electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Preparation and Reactions of Sulfides
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the âOH group. Consequently, the double bond attacks an electrophilic halogen to...
Base-Promoted α-Halogenation of Aldehydes and Ketones
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a Ï bond. In alkynes, the presence of two Ï 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.