Hexafluoroisopropanol: A Powerful Solvent for the Hydrogenation of ­Functionalized Aromatic Compounds

Abstract

Various substituted aromatic compounds have been ­reduced under H₂ using RuCl₃. The fluorous solvent hexafluoro­isopropanol turned out to be particularly efficient in the case of compounds difficult to reduce in organic solvents.

Key words

hydrogenation - aromatic compounds - ruthenium - ­fluorous media - hexafluoroisopropanol

References

• 1 Farrauto RJ. Bartholomew CH. In Fundamentals of Industrial Catalytic Processes   Blackie Academic and Professional; London: 1997. 
• 2 Rabideau PW. Tetrahedron  1989,  45:  1579 
• 3 Nishiki M. Miyataka H. Niino Y. Mitsuo N. Satoh T. Tetrahedron Lett.  1982,  23:  193 
• 4 Rylander PN. In Hydrogenation Methods   Academic Press; New York: 1985. 
• 5 Boxwell CJ. Dyson PJ. Ellis DJ. Welton T. J. Am. Chem. Soc.  2002,  124:  9334 
• 6 Schulz J. Roucoux A. Patin H. Chem.-Eur. J.  2000,  6:  618 
• 7 Bonilla RJ. James BR. Jessop PG. Chem. Commun.  2000,  941 
• 8 Schulz J. Levigne S. Roucoux A. Patin H. Adv. Synth. Catal.  2002,  344:  266 
• 9 Fache F. Lehuede S. Lemaire M. Tetrahedron Lett.  1995,  36:  885 
• 10a Sanchez MA. Mainar AM. Pardo JI. Lopez MC. Urieta JS. Can. J. Chem.  2001,  79:  1460 
• 10b Abe H. Amii H. Uneyama K. Org. Lett.  2001,  3:  313 
• 11 For a very recent review on the use of HFIP see: Bégué JP. Bonnet-Delpon D. Crousse B. Synlett  2004,  18 
• 12 Baitinger WF. von Schleyer P. Mislow K. J. Am. Chem. Soc.  1965,  87:  3168 
• 13 Maiti NC. Carey PR. Anderson VE. J. Phys. Chem.  2003,  107:  9910 

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All the product analyses are in agreement with already published data. [9]