One-pot reductive monoalkylation of nitro aryls with hydrogen over Pd/C

Tetrahedron Letters

Volumn 49, Issue 7, 2008, Pages 1199-1202

  Sydnes, Magne O ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Nitro aryls; One pot; Pd C; Reductive monoalkylation; Secondary alkyl amino aryls

Indexed keywords

ALCOHOL; ALDEHYDE; AMINE; FORMALDEHYDE; HYDROGEN; LEAD; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ALKYLATION; ARTICLE; DEHYDROGENATION; ONE POT SYNTHESIS; REDUCTION;

EID: 38349062190     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.030     Document Type: Article

References (18)

1. Ono N. The Nitro Group in Organic Synthesis (2001), Wiley, New York
2. Ono N. The Nitro Group in Organic Synthesis (2001), Wiley, New York 170-175
3. Salvatore R.N., Yoon C.H., and Jung K.W. Tetrahedron 57 (2001) 7785-7811
4. Xiaojian Z., Zuwang W., Li L., Guijuan W., and Jiaping L. Dyes and Pigments 36 (1998) 365-371
5. Bae J.W., Cho Y.J., Lee S.H., Yoon C.-O.M., and Yoon C.M. Chem. Commun. (2000) 1857-1858
6. Yoon and co-workers later extended the chemistry described in Ref. 5 to the synthesis of tertiary aromatic amines containing two different alkyl groups, see:. Jung Y.J., Bae J.W., Park E.S., Chang Y.M., and Yoon C.M. Tetrahedron 59 (2003) 10331-10338
7. Sajiki H., Ikawa T., and Hirota K. Org. Lett. 6 (2004) 4977-4980
8. Sajiki H., Ikawa T., and Hirota K. Org. Process Res. Dev. 9 (2005) 219-220
9. Nacario R., Kotakonda S., Fouchard D.M.D., Tillekeratne L.M.V., and Hudson R.A. Org. Lett. 7 (2005) 471-474
10. Fouchard D.M.D., Tillekeratne L.M.V., and Hudson R.A. Synthesis (2005) 17-18
11. Reddy C.R., Vijeender K., Bhusan P.B., Madhavi P.P., and Chandrasekhar S. Tetrahedron Lett. 48 (2007) 2765-2768
12. Chandrasekhar S., Narsihmulu Ch., and Jagadeshwar V. Synlett (2002) 771-772
13. Pd/C (10%) used during these experiments was a gift from Kawaken Fine Chemicals.
14. Sydnes, M. O.; Doi, I.; Ohishi, A.; Kuse, M.; Isobe, M. Chem. Asian J. 2008, doi:10.1002/asia.200700211.
15. Ethanol (99.5%) from Wako Pure Chemical Industries, Ltd was used as solvent for these experiments. According to the analytical data sheet provided by the company the ethanol contains <0.001% mass/mass of aldehydes and ketones. This rules out the possibility that acetaldehyde is present in the solvent as a contaminant in high quantity from the start of the reaction.
16. Esaki H., Ohtaki R., Maegawa T., Monguchi Y., and Sajiki H. J. Org. Chem. 72 (2007) 2143-2150
17. 3 requires: C, 65.80; H, 8.07; N, 5.90.
18. 3 requires: C, 64.55; H, 7.67; N, 6.27.