Regio‐ and Stereo‐Selective Ring Opening of Cyclopropenes with Triflic Acid: en Route to Vinyl Triflates

Abstract Herein, we report a triflic acid‐mediated ring opening of cyclopropenes, affording vinyl triflates with high regio‐ and stereo‐selectivity. An intramolecular halogen transfer reactivity was also observed in this reaction, offering a tool to access the valuable vinyl chloride and bromide. The vinyl triflate products are applicable to palladium‐catalyzed cross coupling reactions, delivering various trisubstituted olefins and dienes with moderate yields.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-02-04
DOI
https://doi.org/10.1002/ejoc.202401410
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.00

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article

Regio‐ and Stereo‐Selective Ring Opening of Cyclopropenes with Triflic Acid: en Route to Vinyl Triflates

Qian Wang, Fei Wang, Shanshan Xin
European Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
article

Regio‐ and Stereo‐Selective Ring Opening of Cyclopropenes with Triflic Acid: en Route to Vinyl Triflates

Qian Wang, Fei Wang, Shanshan Xin
article en

Abstract

Abstract Herein, we report a triflic acid‐mediated ring opening of cyclopropenes, affording vinyl triflates with high regio‐ and stereo‐selectivity. An intramolecular halogen transfer reactivity was also observed in this reaction, offering a tool to access the valuable vinyl chloride and bromide. The vinyl triflate products are applicable to palladium‐catalyzed cross coupling reactions, delivering various trisubstituted olefins and dienes with moderate yields.

European Journal of Organic ChemistryVol. 28(13)
Nankai University (CN)
National Natural Science Foundation of China, Nankai University, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 98%
Cyclopropane Reaction Mechanisms
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