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PhenoFluor®Mix, 07-4055: An Air Stable Reagent for Deoxyfluorination

An Efficient Reagent for Selective Deoxyfluorination of Phenols and Aliphatic Alcohols

A powdered mixture of 1,3-Bis(2,6-di-i-propylphenyl)-2-chloroimidazolium chloride (07-0620) and CsF is now available .

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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

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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.201517 (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

07-4055: 1,3-Bis(2,6-di-i-propylphenyl)-2-chloroimidazolium chloride/cesium fluoride admixture (1.0/6.7 molar ratio or 1/2.2 weight ratio) PhenoFluor®Mix, CAS # 1228185-09-8

 

Visit the link below to view related products on our website:

Fluorination and Trifluoromethylation Selected Catalysts and Reagents

 

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