A powdered mixture of 1,3-Bis(2,6-di-i-propylphenyl)-2-chloroimidazolium chloride (07-0620) and CsF is now available .
As a practical alternative to 1,3-Bis(2,6-di-i-propylphenyl)-2,2-difluoroimidazoline, PhenoFluor®Mix (07-4055) is a deoxyfluorinating admixture. Useful for deoxyfluorinating a variety of phenols and aliphatic alcohols,1,2 especially in the pharmaceutical and agrochemical industries, PhenoFluor®Mix can be employed for rapid analogue synthesis. PhenoFluor®Mix overcomes challenges associated with PhenoFluor®. Stable to moisture, the PhenoFluor®Mix is storable in air and can be dried prior to use. The usefulness of the reagent for the deoxyfluorination of a variety of phenols and heterocycles has been recently published.3
Deoxyfluorination with PhenoFluor®Mix is of fundamental interest, as fluorination is observed exclusively even in the presence of two equivalents of chloride. A chemoselective halogenation reaction that proceeds with fluoride, but not with the other halides, is uncommon.4
References:
1) (a) Tang, P.; Wang, W.; Ritter, T. J. Am. Chem. Soc., 2011, 133, 11482 (b) Sladojevich, F.; Arlow, S. I.; Tang, P.; Ritter, T. J. Am. Chem. Soc., 2013, 135, 2470 (c) Campbell, M. G.; Ritter, T. Org. Process Res. Dev., 2014, 18, 474. (d) Fujimoto, T.; Becker, F.; Ritter, T. Org. Process Res. Dev., 2014, 18, 1041.
2) For recent reviews of fluorination, see: (a) Furuya, T.; Klein, J. E. M. N.; Ritter, T. Synthesis 2010, 1804. (b) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature, 2011, 473, 470, (c) Hollingworth, C.; Gouverneur, V. Chem. Commun., 2012, 48, 2929, (d) Jin, Z.; Hammond, G. B.; Xu, B. Aldrichimica Acta 2012, 45, 67 (e) Ruzziconi, R.; Buonerba, F. J. Fluor. Chem., 2013, 152, 12. (f) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem. Int. Ed., 2013, 52, 8214 (g) Brooks, A. F.; Topczewski, J. J.; Ichiishi, N.; Sanford, M. S.; Scott, P. J. H. Chem. Sci., 2014, 5, 4545.
3) Fujimoto, T.; Ritter, T. Org. Lett., 2015, 17 (3), 544–547.
4) For reviews of aryl halide synthesis, see: (a) Vigalok, A. Chem. Eur. J., 2008, 14, 5102
(b) Sheppard, T. D. Org. Biomol. Chem., 2009, 7, 1043. For recent examples of aryl halide synthesis, see: (c) Shen, X.; Hyde, A. M.; Buchwald, S. L. J. Am. Chem. Soc., 2010, 132, 14076
(d) Pan, J.; Wang, X.; Zhang, Y.; Buchwald, S. L. Org. Lett., 2011, 13, 4974 (e) Imazaki, Y.; Shirakawa, E.; Ueno, R.; Hayashi, T. J. Am. Chem. Soc., 2012, 134, 14760.
Products mentioned in this blog:
07-0620: 1,3-Bis(2,6-di-i-propylphenyl)-2-chloroimidazolium chloride, 98+%, CAS # 1228185-09-8
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