Easy-to-Handle Electrophilic Vinylating Reagent

5-Vinyl-5H-thianthren-5-ium Tetrafluoroborate (1) is an electrophilic vinylating reagent, whose structure is a thianthrenium salt substituted by ethylene.^1,2) 1 is a nonhygroscopic solid, so its handling is easy comparing to gas for the vinylation such as vinyl bromide. 1 can be used for various electrophilic vinylations. For example, N-vinylation of nitrogen-containing unsaturated hetero cyclic compounds and Suzuki-Miyaura cross coupling reaction with organoboronic reagents can be carried out. Furthermore, 1 can be used as a Michael acceptor, which leads the synthesis to the synthesis of saturated heterocycles like morpholine.

1 is manufactured under license from Studiengesellschaft Kohle gGmbH. 1 is intended to be used for research and development purposes only. Please contact us if you like to use 1 for commercial purposes or in larger quantities.

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References

• 1) Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene
  • F. Juliá, J. Yan, F. Paulus, T. Ritter, J. Am. Chem. Soc. 2021, 143, 12992.
• 2) Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
  • J. Chen, J. Li, M. B. Plutschack, F. Berger, T. Ritter, Angew. Chem. Int. Ed. 2020, 59, 5616.

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