Chemoselective Reduction of Aldehydes over Ketones with Sodium Tris(hexafluoroisopropoxy)borohydride

Abstract

Chemoselective reduction of aldehydes in the presence of ketones was achieved using sodium tris(hexafluoroisopropoxy)borohydride which can be stored as a THF solution.

Key words

reduction - sodium borohydride - hexafluoroisopropanol - aldehyde - ketone

References and Notes

• 1a Chaikin SW. Brown WG. J. Am. Chem. Soc.  1949,  71:  122 
• 1b Toda F. Kiyoshige K. Yagi M. Angew. Chem., Int. Ed. Engl.  1989,  28:  320 
• 2a Ward DE. Rhee CK. Synth. Commun.  1988,  18:  1927 
• 2b Ward DE. Rhee CK. Can. J. Chem.  1989,  67:  1206 
• 3 Maki Y. Kikuchi K. Tetrahedron Lett.  1977,  263 
• 4 Adams C. Synth. Commun.  1984,  14:  1349 
• 5 Zeynizadeh B. Shirini F. J. Chem. Res., Synop.  2003,  335 
• 6 Tanemura K. Suzuki T. Nishida Y. Satsumabayashi K. Horaguchi T. Synth. Commun.  2005,  35:  867 
• 7 A review on fluorinated alcohols, see: Bégué J.-P. Bonnet-Delpon D. Crousse B. Synlett  2004,  18 
• 8a Golden JH. Schreier C. Singaram B. Williamson SM. Inorg. Chem.  1992,  31:  1533 
• 8b Fuller JC. Karpinski ML. Williamson SM. Singaram B. J. Fluorine Chem.  1994,  66:  123 

9

Analytical Data of Compounds 16 and 17
Compound 16: ^¹H NMR (300 MHz, CDCl₃, TMS): δ = 0.036 (6 H, s), 0.88 (9 H, s), 1.26-1.70 (10 H, m), 2.13 (3 H, s), 2.42 (2 H, t, J = 7.1 Hz), 2.43 (2 H, dt, J = 7.3, 1.8 Hz), 3.65 (1 H, tt, J = 5.6 Hz), 9.77 (1 H, t, J = 1.8 Hz).
Compound 17: ^¹H NMR (300 MHz, CDCl₃, TMS): δ = 0.037 (6 H, s), 0.88 (9 H, s), 1.25-1.68 (13 H, m), 2.13 (3 H, s), 2.42 (2 H, t, J = 7.4 Hz), 3.63 (1 H, m), 3.64 (2 H, t, J = 6.5 Hz).