17 March 2023
Jelgavas iela 1
Europe/Riga timezone

FLUOROHALOMETHYLSULFONIUM SALTS AS A NOVEL FLUOROHALOCARBENE SOURCE

17 Mar 2023, 10:20
20m
109. aud. (Jelgavas iela 1)

109. aud.

Jelgavas iela 1

Speaker

Artūrs Sperga (Latvian Institute of Organic Synthesis)

Description

Synthesis of fluorine containing molecules is of great interest due to its unique properties and vast application in pharmaceuticals, agrochemicals and materials [1].
Previously in our group we have developed fluoromethylene transfer from fluromethylsulfonium salts [2, 3]. Herein we wish to report preliminary results on synthesis of reagents 1 and its initial application in carbene transfer reaction (Scheme 1).

Scheme 1. Alkene cyclopropanation with fluorohalomethylsulfonium salts.
We have found that functionalized sulfonium salts – fluorohalomethylsulfonium reagents 1 are efficient source of fluorhalocarbene under basic conditions and they undergo unactivated alkene 2 cyclopropanation to deliver fluorohalocyclopropanes 3.

References:
[1] Zhou, Y., et al. Chem. Rev. 2016, 116, 422–518.
[2] Melngaile, R., Veliks, J. Synthesis 2021, 53, 4549-4558.
[3] Sperga, A., Zacs, D., Veliks J. Org. Lett. 2022, 24, 4474–4478.

Primary author

Artūrs Sperga (Latvian Institute of Organic Synthesis)

Co-author

Presentation materials