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Visible light-induced thiocyanation of gem-difluorinated phosphonium salts

Gregory Andreevich Lozhkin 1, 2
Gregory Andreevich Lozhkin
Alexey Leonidovich Trifonov 1
Alexey Leonidovich Trifonov
2 Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
Published 2023-06-13
CommunicationVolume 33, Issue 4, 491-493
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Lozhkin G. A., Trifonov A. L., Dilman A. D. Visible light-induced thiocyanation of gem-difluorinated phosphonium salts // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 491-493.
GOST all authors (up to 50) Copy
Lozhkin G. A., Trifonov A. L., Dilman A. D. Visible light-induced thiocyanation of gem-difluorinated phosphonium salts // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 491-493.
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TY - JOUR
DO - 10.1016/j.mencom.2023.06.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.016
TI - Visible light-induced thiocyanation of gem-difluorinated phosphonium salts
T2 - Mendeleev Communications
AU - Lozhkin, Gregory Andreevich
AU - Trifonov, Alexey Leonidovich
AU - Dilman, Alexander Davidovich
PY - 2023
DA - 2023/06/13
PB - Mendeleev Communications
SP - 491-493
IS - 4
VL - 33
ER -
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@article{2023_Lozhkin,
author = {Gregory Andreevich Lozhkin and Alexey Leonidovich Trifonov and Alexander Davidovich Dilman},
title = {Visible light-induced thiocyanation of gem-difluorinated phosphonium salts},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.016},
number = {4},
pages = {491--493},
doi = {10.1016/j.mencom.2023.06.016}
}
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Lozhkin, Gregory Andreevich, et al. “Visible light-induced thiocyanation of gem-difluorinated phosphonium salts.” Mendeleev Communications, vol. 33, no. 4, Jun. 2023, pp. 491-493. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.016.

Keywords

nitrones
organofluorine compounds
phosphonium salts
photochemical reactions.
radicals
thiocyanates

Abstract

gem-Difluorinated phosphonium salts were generated from nitrones by methylation and reaction with (triphenylphosphonio)difluoroacetate. The phosphonium salts were subjected to visible light-induced phosphonium-thiocyanate exchange in the presence of ammonium thiocyanate, copper thiocyanate, and an iridium photocatalyst. The sequence of the reactions was performed in one pot affording thiocyanates attached to the difluoromethylene fragment.

References

.
SHELXT– Integrated space-group and crystal-structure determination
Sheldrick G.M.
Acta Crystallographica Section A: Foundations and Advances, 2015
.
Mercury 4.0: from visualization to analysis, design and prediction
Macrae C.F., Sovago I., Cottrell S.J., Galek P.T., McCabe P., Pidcock E., Platings M., Shields G.P., Stevens J.S., Towler M., Wood P.A.
Journal of Applied Crystallography, 2020
.
OLEX2: a complete structure solution, refinement and analysis program
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography, 2009
.
Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination
Krause L., Herbst-Irmer R., Sheldrick G.M., Stalke D.
Journal of Applied Crystallography, 2015
.
Recent advances in the chemistry of organic thiocyanates.
Castanheiro T., Suffert J., Donnard M., Gulea M.
Chemical Society Reviews, 2016
.
Current Contributions of Organofluorine Compounds to the Agrochemical Industry
Ogawa Y., Tokunaga E., Kobayashi O., Hirai K., Shibata N.
iScience, 2020
.
Frustrated Lewis-Pair-Meditated Selective Single Fluoride Substitution in Trifluoromethyl Groups
Mandal D., Gupta R., Jaiswal A.K., Young R.D.
Journal of the American Chemical Society, 2020
.
Visible-Light-Induced Hydrodifluoromethylation of Alkenes with a Bromodifluoromethylphosphonium Bromide
Lin Q., Xu X., Zhang K., Qing F.
Angewandte Chemie - International Edition, 2015
.
Reactions of gem-Difluorinated Phosphonium Salts Induced by Light
Panferova L.I., Tsymbal A.V., Levin V.V., Struchkova M.I., Dilman A.D.
Organic Letters, 2016
.
Difluoromethylene Phosphabetaine as an Equivalent of Difluoromethyl Carbanion
Levin V.V., Trifonov A.L., Zemtsov A.A., Struchkova M.I., Arkhipov D.E., Dilman A.D.
Organic Letters, 2014
.
Nucleophilic Difluoromethylation Using (Bromodifluoromethyl)trimethylsilane
Trifonov A.L., Zemtsov A.A., Levin V.V., Struchkova M.I., Dilman A.D.
Organic Letters, 2016
.
Light-mediated copper-catalyzed phosphorus/halogen exchange in 1,1-difluoroalkylphosphonium salts
Panferova L.I., Levin V.V., Struchkova M.I., Dilman A.D.
Chemical Communications, 2019
.
Synthesis and decarboxylative Wittig reaction of difluoromethylene phosphobetaine.
Zheng J., Cai J., Lin J., Guo Y., Xiao J.
Chemical Communications, 2013
.
Psammaplins from the Sponge Pseudoceratina purpurea: Inhibition of Both Histone Deacetylase and DNA Methyltransferase
Piña I.C., Gautschi J.T., Wang G., Sanders M.L., Schmitz F.J., France D., Cornell-Kennon S., Sambucetti L.C., Remiszewski S.W., Perez L.B., Bair K.W., Crews P.
Journal of Organic Chemistry, 2003
.
Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept
Toulgoat F., Alazet S., Billard T.
European Journal of Organic Chemistry, 2014
.
DNA Damage by Fasicularin
Dutta S., Abe H., Aoyagi S., Kibayashi C., Gates K.S.
Journal of the American Chemical Society, 2005
.
Shelf-Stable Electrophilic Reagents for Trifluoromethylthiolation
Shao X., Xu C., Lu L., Shen Q.
Accounts of Chemical Research, 2015
.
Visible-Light-Promoted Iododifluoromethylation of Alkenes via (Phosphonio)difluoromethyl Radical Cation
Trifonov A.L., Panferova L.I., Levin V.V., Kokorekin V.A., Dilman A.D.
Organic Letters, 2020
.
Recent Advances in the Synthesis of SCF2H- and SCF2FG-Containing Molecules
Xiong H., Pannecoucke X., Besset T.
Chemistry - A European Journal, 2016
.
Late stage trifluoromethylthiolation strategies for organic compounds
Barata-Vallejo S., Bonesi S., Postigo A.
Organic and Biomolecular Chemistry, 2016
.
Recent progress of direct thiocyanation reactions
Chen H., Shi X., Liu X., Zhao L.
Organic and Biomolecular Chemistry, 2022
.
Interaction of difluoromethylene phosphobetaine with heteroatom-centered electrophiles
Trifonov A.L., Panferova L.I., Levin V.V., Volodin A.D., Korlyukov A.A., Dilman A.D.
Journal of Fluorine Chemistry, 2019
.
The chemistry of thiocyanic esters
Erian A.W., Sherif S.M.
Tetrahedron, 1999
.
Progress on the Synthesis and Applications of Thiocyanates
Xu Q., Zhang L., Feng G., Jin C.
Chinese Journal of Organic Chemistry, 2019