Mild and efficient PtO 2-catalyzed one-pot reductive mono-N-alkylation of nitroarenes

Synthetic Communications

Volumn 42, Issue 17, 2012, Pages 2490-2502

  Sreedhar, Bojja ^a   Rawat, Vikas S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldehyde; Carbonyl compound; Nitroarenes; Platinum dioxide; Protecting group; Reductive amination

Indexed keywords

ALDEHYDE; AROMATIC NITRO COMPOUND; DICHLOROMETHANE; HYDROGEN; METHANOL;

ALKYLATION; AMINATION; ARTICLE; ATMOSPHERIC PRESSURE; CATALYST; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; REACTION OPTIMIZATION; ROOM TEMPERATURE;

EID: 84861969571     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.561397     Document Type: Article

References (46)

1. (a) Gordon, E. M.; Barret, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. Applications of combinatorial technologies to drug discovery, 1: Background and peptide combinatorial libraries. J. Med. Chem. 1994, 37, 1385;
2. (b) Merla, B.; Risch, N. Efficient synthesis of diastereomerically pure 1,3-diamines. Synthesis 2002, 1365;
3. (c) Henkel, T.; Brunne, R. M.; Mueller, H.; Reichel, F. Statistical investigation into the structural complementarity of natural products and synthetic compounds. Angew. Chem. Int. Ed. 1999, 38, 643.
4. Sharp, D. B. Metolachlor. In Herbicides: Chemistry, Degradation, and Mode of Action; P. C. Kearney, D. D. Kaufman (Eds.); Marcel Dekker: New York, 1988; Chapter 7.
5. Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999; p. 789.
6. Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999; p. 835.
7. (a) Lingaiah, N.; Babu, N. S.; Reddy, K. M.; Prasad, P. S. S.; Suryanarayana, I. An efficient reusable silver-exchanged tungstophosphoric acid heterogeneous catalyst for solvent-free intermolecular hydroamination of alkynes. Chem. Commun. 2007, 278;
8. (b) Komeyama, K.; Morimoto, T.; Takaki, K. A simple and efficient iron-catalyzed intramolecular hydroamination of unactivated olefins. Angew. Chem. Int. Ed. 2006, 45, 2938.
9. Hutchins, R. O.; Natale, N. R. Cyanoborohydride: Utility and applications in organic synthesis. Org. Prep. Proced. Int. 1979, 11, 201.
10. Borch, R. F.; Bernstien, M. D.; Durst, H. D. Cyanohydridoborate anion as a selective reducing agent. J. Am. Chem. Soc. 1971, 93, 2897.
11. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride: Studies on direct and indirect reductive amination procedures. J. Org. Chem. 1996, 61, 3849.
12. (a) Bomann, M. D.; Guch, I. C.; DiMare, M. J. A mild, pyridine-borane-based reductive amination protocol. J. Org. Chem. 1995, 60, 5995;
13. (b) Pelter, A.; Rosser, R. M.; Mills, S. Reductive aminations of ketones and aldehydes using borane-pyridine. J. Chem. Soc., Perkin Trans. 1 1984, 717;
14. (c) Moorman, A. E. Reductive amination of piperidines with aldehydes using borane-pyridine. Synth. Commun. 1993, 23, 789.
15. Tarasevich, V. A.; Kozlov, N. G. Reductive amination of oxygen-containing organic compounds. Russ. Chem. Rev. 1999, 68, 55.
16. Micovic, I. V.; Ivanovic, M. D.; Piatak, D. M.; Bojic, V. D. A simple method for preparation of secondary aromatic amines. Synthesis 1991, 1043.
17. Chen, B.-C.; Sundeen, J. E.; Guo, P.; Bednarz, M. S.; Znao, R. Novel triethylsilane-mediated reductive N-alkylation of amines: Improved synthesis of 1-(4-imidazolyl) methyl-4-sulfonylbenzodiazepines, new farnesyltransferase inhibitors. Tetrahedron Lett. 2001, 42, 1245.
18. Suwa, T.; Sugiyama, E.; Shibata, I.; Baba, A. Chemoselective reductive amination of aldehydes and ketones by dibutylchlorotin hydride-HMPA complex. Synthesis 2000, 6, 789.
19. Lee, O. Y.; Law, K. L.; Ho, C.; Yang, Y. D. Highly chemoselective reductive amination of carbonyl compounds promoted by InCl3=Et3SiH=MeOH system. J. Org. Chem. 2008, 73, 8829.
20. Gnanamgari, D.; Moores, A.; Rajaseelan, E.; Crabtree, R. H. Transfer hydrogenation of imines and alkenes and direct reductive amination of aldehydes catalyzed by triazolederived iridium(I) carbene complexes. Organometallics 2007, 26, 1226.
21. Imao, D.; Fujihara, S.; Yamamoto, T.; Ohta, T.; Ito, Y. Effective reductive amination of carbonyl compounds with hydrogen catalyzed by iridium complex in organic solvent and in ionic liquid. Tetrahedron 2005, 61, 6988.
22. Tararov, V. I.; Kadyrov, R.; Riermeierc, T. H.; Borner, A. On the reductive amination of aldehydes and ketones catalyzed by homogeneous Rh(I) complexes. Chem. Commun. 2000, 1867.
23. (a) Lane, C. F. Sodium Cyanoborohydride-A highly selective reducing agent for organic functional groups. Synthesis 1975, 135;
24. (b) Bhattacharyya, S. Reductive amination with zinc borohydride: Efficient, safe route to fluorinated benzylamines. Synth. Commun. 1997, 4265;
25. (e) Ranu, B. C.; Majee, A.; Sarkar, A. One-pot reductive amination of conjugated aldehydes and ketones with silica gel and zinc borohydride. J. Org. Chem. 1998, 63, 370;
26. (f) Bhattacharyya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. C. Selective mono-alkylation of ammonia: A high-throughput synthesis of primary amines. Synlett 1999, 1781;
27. (g) Saxena, I.; Borah, R.; Sarma, J. C. Reductive amination of aromatic aldehydes and ketones with nickel boride. J. Chem. Soc., Perkin Trans. 1 2000, 503.
28. (a) Bhanushali, M. J.; Nandurkar, N. S.; Bhor, M. D.; Bhanage, B. M. Direct reductive amination of carbonyl compounds using bis(triphenylphosphine) copper(I) tetrahydroborate. Tetrahedron Lett. 2007, 48, 1273;
29. (b) Robichaud, A.; Ajjou, A. N. First example of direct reductive amination of aldehydes with primary and secondary amines catalyzed by water-soluble transition-metal catalysts. Tetrahedron Lett. 2006, 47, 3633;
30. (c) Sato, S.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. One-pot reductive amination of aldehydes and ketones with a-picoline-borane in methanol, in water, and in neat conditions. Tetrahedron 2004, 60, 7899.
31. 14. Chem. Commun. 2000, 1857.
32. Byun, E.; Hong, B.; De Castro, K. A.; Lim, M.; Rhee, H. One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes. J. Org. Chem. 2007, 72, 9815.
33. Sydnes, M. O.; Kuse, M.; Isobe, M. Reductive monoalkylation of nitro aryls in one pot. Tetrahedron 2008, 64, 6406.
34. Sreedhar, B.; Reddy, P. S.; Devi, D. K. Direct one-pot reductive amination of aldehydes with nitroarenes in a domino fashion: Catalysis by gum-acacia-stabilized palladium nanoparticles. J. Org. Chem. 2009, 74, 8806.
35. Sreedhar, B.; Reddy, P. S.; Reddy, M. A.; Neelima, B.; Arundhathi, R. AgOTf-catalyzed direct amination of benzyl alcohols with sulphonamides. Tetrahedron Lett. 2007, 46, 8174.
36. Hudlicky, M. Reductions in Organic Chemistry; John Wiley and Sons: New York, 1984; p. 11.
37. March, J. Advanced Organic Chemistry, 4th ed.; John Wiley and Sons: New York, 1992; p. 881.
38. Hudlicky, M. Reductions in Organic Chemistry; John Wiley and Sons: New York, 1984; p. 53.
39. Takasaki, M.; Motoyama, Y.; Higashi, K.; Yoon, S. H.; Mochida, I.; Nagashima, H. Chemoselective hydrogenation of nitroarenes with carbon nanofiber-supported platinum and palladium nanoparticles. Org. Lett. 2008, 10, 1601.
40. (a) Cho, B. T.; Kang, S. K. Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions. Tetrahedron 2005, 61, 5725-5734;
41. (b) Liao, W.; Chen, Y.; Liu, Y.; Duan, H.; Petersena, J. L.; Shi, X. 1,2,3-Triazole-boranes: Stable and efficient reagents for ketone and aldehyde reductive amination in organic solvents or in water. Chem. Commun. 2009, 6436-6438;
42. (c) He, R.; Toy, P. H.; Lama, Y. Polymer-supported hantzsch 1,4-dihydropyridine ester: An efficient biomimetic hydrogen source. Adv. Synth. Catal. 2008, 350, 54-60.
43. (a) Zhang, H.; Cai, Q.; Ma, D. Amino acid-promoted cui-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles. J. Org. Chem. 2005, 70, 5164-5173;
44. (b) Yang, C. T.; Fu, Y.; Huang, Y. B.; Yi, J.; Guo, Q. X.; Liu, L. Room-temperature copper-catalyzed carbon-nitrogen coupling of aryl iodides and bromides promoted by organic ionic bases. Angew. Chem. Int. Ed. 2009, 48, 7398-7401.
45. Ulgen, M.; Gorrod, J. W. Microsomal formation of N-benzyl-4- hydroxymethylaniline from N-benzyl-4-methylaniline. J. Pharm. Pharmacol. 1992, 865-866.
46. (a) Zhu, X.; Su, L.; Huang, L.; Chen, G.; Wang, J.; Song, H.; Wan, Y. A facile and efficient oxalyldihydrazide=ketone-promoted copper-catalyzed amination of aryl halides in water. Eur. J. Org. Chem. 2009, 635-642.