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Pentafluorosulfanyl (SF5) Compounds

SF5 Compounds, the Best Alternative to CF3

SF5 Compounds1)2) also known as “Super CF3 group”, are building blocks for Pharmaceutical, Agrochemical and Material Science applications.

Main Properties

High Thermal and Chemical Stability3)4)

> Strong alkaline condition

» No decomposition in NaOH
(solution in water /EtOH) at reflux temperature)

> Strong acidic condition

» No decomposition in conc. H2SO4 at room temperature
» Almost no hydrolysis in 100% H2SO4 at 100ºC (Ph-CF3 is hydrolyzed at 95ºC in same condition)

> Thermal stability

» Almost no decomposition at 400ºC (in a glass tube)

Strong Electron-withdrawing Effect3)

Outstanding Lipophilicity5)

Lipophilicity(π) of substituent X

Physical Size of SF53)

Electrostatic Potential Maps6)

1) Umemoto, T.; Garrick, L. M.; Saito N. Beilstein J. Org. Chem. 2012, 8, 461.
2) Kosobokov, M.; Cui, B.; Balia, A.; Matsuzaki, K.; Tokunaga, E.; Saito N.; Shibata, N. Angew. Chem Int. Ed. Engl. 2016, 55, 10781.
3) Sheppard, W. A. J. Am. Chem. Soc. 1962, 84. 3072.
4) a) Bowden, R. D.; Comina, P. J.; Greenhall, M. P.; Kariuki, B. M.; Loveday, A.; Philip D. Tetrahedron 2000, 56, 3399.
b) Kirsch, P.; Bremer, M.; Heckmeier, M.; Tarumi, K. Angew. Chem Int. Ed. Engl. 1999, 38, 1989.
5) Kirsch, P. Modern Fluoroorganic Chemistry. Weinheim, Germany: Wiley-VCH 2004, 146.
6) Westphal, M. V.; Wolfstädter, B. T.; Plancher, J. M.; Gatfield, J.; Carreira, E. M. Chem. Med. Chem. 2015, 10, 461.


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