Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2‑Bromoethyl)diphenylsulfonium Triflate

The potential of (2-bromoethyl)­diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes i...

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Bibliographic Details
Published in:Organic letters 2021-09, Vol.23 (17), p.6795-6800
Main Authors: Ming, Xiao-Xia, Wu, Shuai, Tian, Ze-Yu, Song, Jia-Wei, Zhang, Cheng-Pan
Format: Article
Language:English
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Summary:The potential of (2-bromoethyl)­diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes in moderate to excellent yields. This protocol represents the first application of (2-haloethyl)­diphenylsulfonium triflate as a CHCH2 transfer source in organic synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02379