Study on the selective reductive animation of aromatic aldehydes in ionic liquids

Gao Xiao Hua Xue Gong Cheng Xue Bao/Journal of Chemical Engineering of Chinese Universities

Volumn 20, Issue 2, 2006, Pages 306-309

  Luo, Shu Ping ^a   Xu, Dan Qian ^a   Zhang, Fan ^a   Yang, Wen Long ^a   Liu, Bao You ^a   Du, Xiao Hua ^a   Xu, Zhen Yuan ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Amine; Aromatic aldehyde; Ionic liquids; Reductive animation; Sodium borohydride

Indexed keywords

AMINES; AROMATIC COMPOUNDS; BORON COMPOUNDS; CONDENSATION REACTIONS; IONIZATION OF LIQUIDS; REDUCTION; SODIUM COMPOUNDS; SOLVENTS;

AROMATIC ALDEHYDE; IONIC LIQUIDS; REDUCTIVE ANIMATION; SODIUM BOROHYDRIDE;

ALDEHYDES;

EID: 33745125672     PISSN: 10039015     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. Zhao D B, Wu M, Kou Y, et al. Ionic liquids: applications in catalysis[J]. Catalysis Today, 2002, 74(2): 157-189
2. SHEN Run-pu, PI Shi-qing, XIA Wei, et al. Synthesis of 3-aminopyrrolidine and its N-alkylating derivatives[J]. J Chem Eng of Chinese Univ, 2003, 17(4): 438-441
3. Nagarajan S, Ganem B. Chemistry of naturally occurring polyamines. 11. Unsaturated spermidine and spermine derivatives[J]. J Org Chem, 1987, 52(22): 5044-5046.
4. Wrobel J E, Ganem B. A general, highly stereoselective synthesis of amines[J]. Tetrahedron Lett. 1981, 22(36): 3447-3450.
5. Borch R F, Bernstein M D, Durst H D. Cyanohydridoborate anion as a selective reducing agent[J]. J Am Chem Soe, 1971, 93(12): 2897-2904.
6. Pelter A, Rosser R M, Mills S. Reductive amination of ketones and aldehydes using borane-pyridine[J]. J Chem Soc, Perkin Transl, 1984: 717-720.
7. Yoon N M, Kim E G, Son H S, et al. Borohydride exchange resin. A new reduction agent for reductive amination[J]. Synth Commun, 1993, 23(11): 1595-1599.
8. Verardo G, Giumanini A G, Strazzolini P, Poiana M. Reductive N-monoalkylation of primary aromatic amines[J]. Synthesis, 1993, (1): 121-125.
9. Mattson R J, Pham K M, Leuck D J, et al. An improved method for reductive alkylation of amines using titanium (IV) isopropoxide and sodium cyanoborohydride[J]. J Org Chem, 1990, 55(8): 2552-2554.
10. Bhattacharyya S, Chatterjee A, Duttachowdhury S K. Use of zinc borohydride in reductive amination: an efficient and mild method for N-methylation of amines[J]. J Chem Soc, Perkin Trans 1, 1994, (1): 1-2.
11. Kim S, Oh C H, Ko J S, et al. Zinc-modified cyanoborohydride as a selective reducing agent[J]. J Org Chem, 1985, 50(11): 1927-1932.
12. Ira S, Ruli B, Jadab C S. Reductive amination of aromatic aldehydes and ketones with nikel boride[J]. J Chem Soc, Perkin Trans 1, 2000, (4): 503-504.
13. Abdel-Magid A F, Carson K G, Harris B D, et al. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures[J]. J Org Chem, 1996, 61(11): 3849-3862.
14. Ranu B C, Majee A, Sarkar A. One-pot reductive amination of conjugated aldehydes and ketones with silica gel and zinc borohydride[J]. J Org Chem, 1998, 63(2): 370-373.
15. Sukanta B, Sunki R, Owen W G, et al. Polymer-supported triacetoxyborohydride: A novel reagent of choice for reductive amination[J]. Tetrahedron Lett, 2003, 44(27): 4957-4960.
16. Rajender S V, Rajender D. Sodium borohydride on wet clay: Solvent-free reductive amination of carbonyl compounds using microwaves[J]. Tetrahedron, 1998, 54(23): 6293-6298.
17. Mariappan P, Muniappan T. Methods of enhancement of reactivity and selectivity of sodium borohydride for applications in organic synthesis[J]. J Organometallic Chem, 2000, 609(2): 137-151.
18. 6[J]. Synth Commun, 2001, 31(19): 2935-2938.
19. XU Dan-qian, LUO Shu-ping, LIU Bao-you, et al. Ambient ionic liquids used in the reduction of aldehydes and ketones[J]. Chin Chem Lett, 2004, 15(6): 643-645
20. Bongote P, Dias A P, Papageorgiou N, et al. Hydrophobic, highly conductive ambient-temperature molten salts[J]. Inorg Chem, 1996, 35(5): 1168-1178.
21. Suarez P A Z, Dullius J E L, Souza R F de, et al. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes[J]. Polyhedron, 1996, 15(7): 1217-1219.
22. Xu D Q, Liu B Y, Luo S P, et al. A novel and eco-friendly method for the preparation of ionic liquids[J]. Synthesis, 2003, (17): 2626-2628.
23. XU Dan-qian, LUO Shu-ping, LIU Bao-you, et al. Catalytic synthesis of benzyl cinnamate in room temperature ionic liquid[J]. Chin J Org Chem, 2004, 24(1): 99-102.