An environmentally benign electrochemical process for the reduction of carboxylic acid hydrazides to amides

Synthesis

Volumn , Issue 9, 2009, Pages 1463-1468

  Mentel, Matthias ^a   Beier, Matthias J ^a   Breinbauer, Rolf ^a,b  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Amides; Electroorganic synthesis; Hydrazides; Reduction; Tin

Indexed keywords

COMPLEX MOLECULES; ELECTROCHEMICAL PROCESS; ELECTROORGANIC SYNTHESIS; ENVIRONMENTALLY BENIGN; EXISTING METHOD; HYDRAZIDES; OLEFINIC GROUPS; ORGANIC SYNTHESIS; PRIMARY AMIDES; REACTION CONDITIONS;

AMIDES; CARBOXYLIC ACIDS; ELECTRIC BATTERIES; ELECTROLYTIC CELLS; ORGANIC ACIDS; TIN;

REDUCTION;

AMIDE; BIPHENYL; CARBOXYLIC ACID; HYDRAZIDE DERIVATIVE; LITHIUM; MERCURY; SODIUM;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PH MEASUREMENT; REDUCTION; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 67650084348     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088164     Document Type: Article

References (80)

1. For an introduction to electroorganic synthesis, see: (a) Torii, S. Electroorganic Reduction Synthesis, Vols. 1 and 2; Kodansha: Tokyo, 2006.
2. (b) Organic Electrochemistry, 4th ed.; Lund, H.; Hammerich, O., Eds.; Marcel Dekker: New York, 2001.
3. (c) Electroorganic Synthesis; Little, R. D.; Weinberg, N. L., Eds.; Marcel Dekker: New York, 1991.
4. Hoormann, D.; Jörissen, J.; Pütter, H. Chem.-Ing.-Tech. 2005, 77, 1363.
5. For recent reviews, see: (a) Yoshida, J.-i.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008, 108, 2265.
6. (b) Sperry, J. B.; Wright, D. L. Chem. Soc. Rev. 2006, 35, 605.
7. (c) Little, R. D.; Moeller, K. D. Electrochem. Soc. Interface 2002, 11, 28.
8. (d) Moeller, K. D. Tetrahedron 2000, 56, 9527.
9. For selected recent examples, see: (e) Barjau, J.; Königs, P.; Kataeva, O.; Waldvogel, S. R. Synlett 2008, 15, 2309.
10. (f) Xu, H.-C.; Brandt, J. D.; Moeller, K. D. Tetrahedron Lett. 2008, 49, 3868.
11. (g) Tang, F.; Chen, C.; Moeller, K. D. Synthesis 2007, 21, 3411.
12. (h) Wu, H.; Moeller, K. D. Org. Lett. 2007, 9, 4599.
13. (i) Malkowsky, I. M.; Griesbach, U.; Pütter, H.; Waldvogel, S. R. Eur. J. Org. Chem. 2006, 4569.
14. (j) Malkowsky, I. M.; Rommel, C. E.; Fröhlich, R.; Griesbach, U.; Pütter, H.; Waldvogel, S. R. Chem. Eur. J. 2006, 12, 7482.
15. (k) Miller, A. K.; Hughes, C. C.; Kennedy-Smith, J. J.; Gradl, S. N.; Trauner, D. J. Am. Chem. Soc. 2006, 128, 17057.
16. (l) Hughes, C. C.; Miller, A. K.; Trauner, D. Org. Lett. 2005, 7, 3425.
17. (m) Sperry, J. B.; Wright, D. L. J. Am. Chem. Soc. 2005, 127, 8034.
18. (n) Girard, N.; Hurvois, J.-P.; Moinet, C.; Toupet, L. Eur. J. Org. Chem. 2005, 2269.
19. (o) Liu, B.; Duan, S.; Sutterer, A. C.; Moeller, K. D. J. Am. Chem. Soc. 2002, 124, 10101.
20. (p) Chai, D.; Genders, D.; Weinberg, N.; Zappi, G.; Bernasconi, E.; Lee, J.; Roletto, J.; Sogli, L.; Walker, D.; Martin, C. R.; Menon, V.; Zelenay, P.; Zhang, H. Org. Process Res. Dev. 2002, 6, 178.
21. (a) Nad, S.; Breinbauer, R. Synthesis 2005, 20, 3654.
22. (b) Nad, S.; Breinbauer, R. Angew. Chem. Int. Ed. 2004, 43, 2297;
23. Angew. Chem. 2004, 116, 2347.
24. (c) Mentel, M.; Breinbauer, R. Eur. J. Org. Chem. 2007, 4283.
25. For an example, see: Kadow, J. F.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1989, 30, 3299.
26. Ing, H. R.; Manske, R. H. F. J. Chem. Soc. 1926, 2348.
27. Chan, W. C.; Bycroft, B. W.; Evans, D. J.; White, P. D. J. Chem. Soc., Chem. Commun. 1995, 2209.
28. Bycroft, B. W.; Chan, W. C.; Chhabra, S. R.; Hone, N. D. J. Chem. Soc., Chem. Commun. 1993, 778.
29. (a) Feuer, H.; Bachman, G. B.; White, E. H. J. Am. Chem. Soc. 1951, 73, 4716.
30. (b) Ainsworth, C. J. Am. Chem. Soc. 1954, 76, 5774.
31. (c) Hinman, R. L. J. Am. Chem. Soc. 1957, 22, 148.
32. (d) Cagnoli, R.; Ghelfi, F.; Pagnoni, U. M.; Parsons, A. F.; Schenetti, L. Tetrahedron 2003, 59, 9951.
33. Pérez Luna, A.; Ceschi, M.-A.; Bonin, M.; Micouin, L.; Husson, H.-P. J. Org. Chem. 2002, 67, 3522.
34. Guerra, F. M.; Mish, M. R.; Carreira, E. M. Org. Lett. 2000, 2, 4265.
35. (a) Kemp, D. S.; Sidell, M. D.; Shortridge, T. J. J. Org. Chem. 1979, 44, 4473.
36. (b) Mellor, J. M.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1984, 2927.
37. (c) Jacobi, P. A.; Martinelli, M. J.; Polanc, S. J. Am. Chem. Soc. 1984, 106, 5594.
38. (d) Gilchrist, T. L.; Hughes, D.; Wasson, R. Tetrahedron Lett. 1987, 28, 1573.
39. (e) Meng, Q.; Hesse, M. Synlett 1990, 148.
40. (f) Koohang, A.; Stanchina, C. L.; Coates, R. M. Tetrahedron 1999, 55, 9669.
41. (g) Wasserman, H. H.; Matsuyama, H.; Robinson, R. P. Tetrahedron 2002, 58, 7177.
42. (a) Vedejs, E.; Meier, G. P. Tetrahedron Lett. 1979, 43, 4185.
43. (b) Denmark, S. E.; Nicaise, O.; Edwards, J. P. J. Org. Chem. 1990, 55, 6219.
44. (c) Brimble, M. A.; Heathcock, C. H. J. Org. Chem. 1993, 58, 5261.
45. (d) Enders, D.; Tiebes, J.; De Kimpe, N.; Keppens, M.; Stevens, C.; Smagghe, G.; Betz, O. J. Org. Chem. 1993, 58, 4881.
46. (e) Enders, D.; Leriverend, C. Tetrahedron: Asymmetry 1997, 8, 2787.
47. Atkinson, R. S.; Edwards, P. J.; Thomson, G. A. J. Chem. Soc., Perkin Trans. 1 1994, 3209.
48. (a) Atkinson, R. S.; Kelly, B. J.; Williams, J. Tetrahedron 1992, 48, 7713.
49. (b) Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266.
50. (c) Burk, M. J.; Martinez, J. P.; Feaster, J. E.; Cosford, N. Tetrahedron 1994, 50, 4399.
51. (d) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447.
52. (e) Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159.
53. (f) Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942.
54. (g) Enders, D.; Funabiki, K. Org. Lett. 2001, 3, 1575.
55. (h) Ding, H.; Friestad, G. K. Org. Lett. 2004, 6, 637.
56. (i) Friestad, G. K. Eur. J. Org. Chem. 2005, 3157.
57. Souppe, J.; Danon, L.; Namy, J. L.; Kagan, H. B. J. Organomet. Chem. 1983, 250, 227.
58. Horner, L.; Jordan, M. Liebigs Ann. Chem. 1978, 1505.
59. Vera, J.; Martinez-Ortiz, F.; Ripoll, A. Electrochim. Acta 1986, 31, 1231.
60. Chauveau, A.; Martens, T.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2002, 1885.
61. Laboratory Techniques in Electroanalytical Chemistry, 2nd ed.; Kissinger, P. T.; Heineman, W. R., Eds.; Marcel Dekker: New York, 1996.
62. (a) Kelber, C. Ber. Dtsch. Chem. Ges. 1921, 54, 2255.
63. (b) Kämmerer, H.; Horner, L.; Beck, H. Chem. Ber. 1958, 91, 1376.
64. Desai, K. G.; Desai, K. R. Molbank 2006, M477.
65. Butler, R. N.; Hanniffy, J. M.; Stephens, J. C.; Burke, L. A. J. Org. Chem. 2008, 73, 1354.
66. Bowman, W. R.; Forshaw, J. A.; Hall, K. P.; Kitchin, J. P.; Mott, A. W. Tetrahedron 1996, 52, 3961.
67. Bernhardt, P. V.; Chin, P.; Richardson, D. R. J. Biol. Inorg. Chem. 2001, 6, 801.
68. Zhang, X.; Breslav, M.; Grimm, J.; Guan, K.; Huang, A.; Liu, F.; Maryanoff, C. A.; Palmer, D.; Patel, M.; Qian, Y.; Shaw, C.; Sorgi, K.; Stefanick, S.; Xu, D. J. Org. Chem. 2002, 67, 9471.
69. Katritzky, A. R.; Wang, M.; Zhang, S. ARKIVOC 2001, (ix), 19.
70. McElvain, S. M.; Starn, R. E. Jr. J. Am. Chem. Soc. 1955, 77, 4571.
71. Breslau, R.; Anderson, M. O.; Rivera, F.; Jimenez, A.; Haddad, T.; Axon, J. R. Tetrahedron 2002, 58, 5513.
72. Al Jammaz, I.; Al-Otaibi, B.; Okarvi, S.; Amartey, J. J. Labelled Compd. Radiopharm. 2006, 49, 125.
73. Taylor, E. C.; Hinkle, J. S. J. Org. Chem. 1987, 52, 4107.
74. Peng, Y.; Song, G. J. Chem. Res. 2003, 768.
75. Milić, D. R.; Opsenica, D. M.; AdnaCrossed d signević, B.; Šolaja, B. A. Molecules 2000, 5, 118.
76. Kuang, L.; Zhou, J.; Chen, S.; Ding, K. Synthesis 2007, 3129.
77. Owston, N. A.; Parker, A. J.; Williams, J. M. J. Org. Lett. 2007, 9, 73.
78. Kergomard, A.; Renard, M. F. Agric. Biol. Chem. 1986, 50, 2913.
79. Bonne, D.; Dekhane, M.; Zhu, J. J. Am. Chem. Soc. 2005, 127, 6926.
80. Shaikh, N. S.; Junge, K.; Beller, M. Org. Lett. 2007, 9, 5429.