Deoxygenation of Aldehydes and Ketones Using Dichloro Bis(1,4-diazabicyclo[2.2.2]octane)(tetrahydroborato) Zirconium(IV)

Abstract

Saturated aldehydes and ketones are converted via their p-toluenesulfonyl hydrazones to the corresponding alkanes using dichloro bis(1,4-diazabicyclo[2.2.2]octane)(tetrahydroborato) zirconium(IV) (ZrBDC). The reactions were performed in DMF-sulfolane at 110 °C and gave the corresponding alkanes in high yields. Regioselectivity in the reduction of α,β-unsaturated carbonyl groups was also observed.

Key words

ZrBDC - tosylhydrazones - reduction - carbonyl compounds - alkanes

References

• 1 Mitchell RH. Lia YH. Tetrahedron Lett.  1980,  2637 
• 2a Lau CK. Dufresne C. Belanger PC. Pietre S. Kim J. J. Org. Chem.  1986,  51:  3038 
• 2b Srikrishna A. Viswajanani R. Sattigeri JA. Yelamaggad CV. Synlett  1995,  93 
• 2c Srikrishna A. Viswajanani R. Sattigeri JA. Yelamaggad CV. Tetrahedron Lett.  1995,  36:  2347 
• 3 Hatano B. Tagaya H. Tetrahedron Lett.  2003,  6331 
• 4a Beh HM. Vanderslice CW. Spehar A. J. Org. Chem.  1969,  34:  3923 
• 4b Hutchins RO. Hoke D. Keogh J. Koharski D. Tetrahedron Lett.  1969,  3495 
• 5a Jacobus J. J. Chem. Soc., Chem. Commun.  1970,  338 
• 5b Maryanoff BE. Milewski CA. J. Chem. Soc., Chem. Commun.  1971,  1097 
• 6a Minlon H. J. Am. Chem. Soc.  1948,  70:  2802 
• 6b Furrow ME. Myers AG. J. Am. Chem. Soc.  2004,  126:  5436 
• 7 Caglioti SL. Tetrahedron  1966,  22:  487 
• 8a Hutchins RO. Milewski G. Maryanoff B. J. Am. Chem. Soc.  1973,  95:  3662 
• 8b Hutchins RO. Kacher M. Rua L. J. Org. Chem.  1975,  40:  923 
• 9 Lau K. Dufresne C. Belanger C. Pietre S. Scheigetz J. J. Org. Chem.  1986,  51:  3038 
• 10 Kim S. Oh CH. Ko JS. Ahn KH. Kin YJ. J. Org. Chem.  1985,  50:  1927 
• 11 Marks TJ. Kolb JR. Chem. Rev.  1977,  77:  263 
• 12a Firouzabadi H. Iranpoor N. Alinezhad H. Synth. Commun.  2002,  32:  3586 
• 12b Firouzabadi H. Iranpoor N. Alinezhad H. Bull. Chem. Soc. Jpn.  2003,  76:  143 
• 13 Meskens FA. Synthesis  1981,  501