Related Experiment Video
Updated: Oct 13, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis of β-cyanoalkylsulfonylated vinyl selenides through a four-component reaction
Fu-Sheng He1, Yanfang Yao1,2, Zhimei Tang1
1School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, China. jie_wu@fudan.edu.cn.
Abstract:
A mild copper-catalyzed four-component selenosulfonylation of alkynes, cycloketone oxime esters, DABCO (SO2)2 and diselenides has been developed. This method enables the rapid assembly of β-cyanoalkylsulfonylated vinyl selenides in moderate to good yields. Advantages of this protocol include a broad substrate scope, good functional group tolerance and the late-stage functionalization of complex molecules. Moreover, the potential utility of this methodology is demonstrated through simple oxidation of the products to access synthetically important alkynyl sulfones. Mechanistic studies suggest that a cyanoalkylsulfonyl radical intermediate is involved in this process.
More Related Videos
05:34Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Related Concept Videos
Preparation and Reactions of Sulfides
Electrophilic Addition to Alkynes: Hydrohalogenation
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
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.