Self-modulated highly chemoselective direct-reductive-amination (DRA) of benzaldehydes straightforward to N-monosubstituted benzylamine hydrochlorides

Tetrahedron

Volumn 64, Issue 51, 2008, Pages 11783-11788

  Xing, Lixin ^a   Cheng, Chuanjie ^a   Zhu, Rui ^a   Zhang, Boyang ^a   Wang, Xinyan ^a   Hu, Yuefei ^a  

^a Tsinghua University   (China)

Author keywords

Amination; Benzylamine; Chemoselectivity; Hydrogenation; Palladium

Indexed keywords

AMINE; BENZALDEHYDE DERIVATIVE; BENZYLAMINE; CARBON; LEAD;

ADDITION REACTION; AMINATION; ARTICLE; ATMOSPHERIC PRESSURE; CATALYSIS; CHEMICAL BOND; HYDROGENATION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 55549108656     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.072     Document Type: Article

References (36)

1. Baxter E.W., and Reitz A.B. Org. React. 59 (2002) 1-714
2. Nishimura S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis (2001), John Wiley & Sons, New York, NY Chapter 6, pp 236-241
3. Chien T.-C., Meade E.A., Hinkley J.M., and Townsend L.B. Org. Lett. 6 (2004) 2857-2859
4. Rosenstrom U., Skold C., Lindeberg G., Botros M., Nyberg F., Karlen A., and Hallberg A. J. Med. Chem. 47 (2004) 859-870
5. Diaz-Gavilan M., Rodriguez-Serrano F., Gomez-Vidal J.A., Marchal J.A., Aranega A., Gallo M.A., Espinosa A., and Campos J.M. Tetrahedron 60 (2004) 11547-11557
6. Moreau A., Couture A., Deniau E., and Grandclaudon P. Tetrahedron 62 (2006) 5787-5790
7. Chrzanowska M., Dreas A., and Rozwadowska M.D. Tetrahedron: Asymmetry 16 (2005) 2954-2958
8. Ioanoviciu A., Antony S., Pommier Y., Staker B.L., Stewart L., and Cushman M. J. Med. Chem. 48 (2005) 4803-4814
9. Głuszyńska A., and Rozwadowska M.D. Tetrahedron: Asymmetry 15 (2004) 3289-3295
10. Larghi E.L., and Kaufman T.S. Tetrahedron Lett. 38 (1997) 3159-3162
11. Shirasaka T., Takuma Y., Shimpuku T., and Imaki N. J. Org. Chem. 55 (1990) 3767-3771
12. Kruse L.I., Kaiser C., DeWolf W.E., Frazee Jr. J.S., Garvey E.E., Hilbert L., Faulkner W.A., Flaim K.E., Sawyer J.L., and Berkowitz B.A. J. Med. Chem. 29 (1986) 2465-2472
13. Mitscher L.A., Gill H., Filppi J.A., and Wolgemuth R.L. J. Med. Chem. 29 (1986) 1277-1281
14. Bates H.A., and Garelick J.S. J. Org. Chem. 49 (1984) 4552-4555
15. Frutos R.P., Gallou I., Reeves D., Xu Y., Krishnamurthy D.C., and Senanayake H. Tetrahedron Lett. 46 (2005) 8369-8372
16. Botta M., Corelli F., Gasparrini F., Messina F., and Mugnaini C. J. Org. Chem. 65 (2000) 4736-4739
17. Wang T., and Cloudsdale I.S. Synthesis (2000) 265-268
18. Guarna A., Guidi A., Machetti F., Menchi G., Occhiato E.G., Scarpi D., Sisi S., and Trabocchi A. J. Org. Chem. 64 (1999) 7347-7364
19. Campbell A.D., Raynham T.M., and Taylor R.J.K. Chem. Commun. (1999) 245-246
20. Zimmerman S.C., and Duerr B.F. J. Org. Chem. 57 (1992) 2215-2217
21. Kruse L.I., Kaiser C., DeWolf W.E., Finkelstein J.A., Frazee J.S., Hilbert E.L., Ross S.T., Flaim K.E., and Sawyer J.L. J. Med. Chem. 33 (1990) 781-789
22. Ross S.T., Kruse L.I., Ohlstein E.H., Erickson R.W., Ezekiel M., Flaim K.E., Sawyer J.L., and Berkowitz B.A. J. Med. Chem. 30 (1987) 1309-1313
23. Chan C., Heid R., Zheng S., Guo J., Zhou B., Furuuchi T., and Danishefsky S.J. J. Am. Chem. Soc. 127 (2005) 4596-4598
24. Zhou B., Guo J., and Danishefsky S.J. Org. Lett. 4 (2002) 43-46
25. Scott J.D., and Williams R.M. J. Am. Chem. Soc. 124 (2002) 2951-2956
26. Doshi H., Cardis A.B., Crelling J.K., Miller S.I., Dalton D.R., Zacharias D.E., and Glusker J.P. J. Org. Chem. 52 (1987) 2604-2608
27. Bobbitt J.M., Kulkarni C.L., Dutta C.P., Kofod H., and Chiong K.N. J. Org. Chem. 43 (1978) 3541-3544
28. Imao D., Fujihara S., Yamamoto T., Ohta T., and Ito Y. Tetrahedron 61 (2005) 6988-6992
29. Robichaud A., and Ajjou A.N. Tetrahedron Lett. 47 (2006) 3633-3636
30. Cheng C., Wang X., Xing L., Liu B., Zhu R., and Hu Y. Adv. Synth. Catal. 349 (2007) 1775-1780
31. It is well known that Pd-C catalyzed hydrogenation is enhanced by a catalytic amount of HCl, but retarded with an excess amount of HCl due to the unproductive occupation of Pd-C catalytic sites by HCl molecules.
32. Nishimura S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis (2001), John Wiley & Sons, New York, NY Charter 2, pp 53-59
33. Reviews for hydrodechlorination of chloroalkanes:
34. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 102 (2002) 4009-4092
35. Nishimura S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis (2001), John Wiley & Sons, New York, NY Chart 13, pp 623-639
36. Rylander P.N. Hydrogenation Methods (1985), Academic, London Charter 12, pp 148-156