Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones

Advanced Synthesis and Catalysis

Volumn 354, Issue 14-15, 2012, Pages 2659-2664

  Miao, Wenjun ^a   Gao, Yuzhen ^a   Li, Xueqin ^a   Gao, Yuxing ^a   Tang, Guo ^a   Zhao, Yufen ^b  

^a XIAMEN UNIVERSITY   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

Alkylphosphonates; Carbonyl compounds; Copper catalysis; H phosphonates; N tosylhydrazones

Indexed keywords

EID: 84869007200     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200295     Document Type: Article

References (69)

1. For reviews, see: a) S. Van der Jeught, C. V. Stevens, Chem. Rev. 2009, 109, 2672-2702;
2. b) C. S. Demmer, N. Krogsgaard-Larsen, L. Bunch, Chem. Rev. 2011, 111, 7981-8006;
3. c) L. Coudray, J. L. Montchamp, Eur. J. Org. Chem. 2008, 3601-3613.
4. For a review, see: The Chemistry of Organophosphorous Compounds, (Ed.: F. H. Hartley), Wiley, New York, 1996.
5. a) T. S. Kumar, S.-Y. Zhou, B. V. Joshi, R. Balasubramanian, T. Yang, B. T. Liang, K. A. Jacobson, J. Med. Chem. 2010, 53, 2562-2576;
6. b) P. Lassaux, M. Hamel, M. Gulea, H. Delbrück, P. S. Mercuri, L. Horsfall, D. Dehareng, M. L. Kupper, J.-M. Frére, K. Hoffmann, M. Galleni, C. Bebrone, J. Med. Chem. 2010, 53, 4862-4876.
7. a) Y. Iwase, K. Kamada, K. Ohta, K. Kondo, J. Mater. Chem. 2003, 13, 1575-1581;
8. b) J. F. Hulvat, M. Sofos, K. Tajima, S. I. Stupp, J. Am. Chem. Soc. 2005, 127, 366-372;
9. c) B. W. Messmore, J. F. Hulvat, E. D. Sone, S. I. Stupp, J. Am. Chem. Soc. 2004, 126, 14452-14458;
10. d) C. W. Wu, H. C. Lin, Macromolecules 2006, 39, 7985-7997;
11. e) X. H. Ma, F. Ma, Z. H. Zhao, N. H. Song, J. P. Zhang, J. Mater. Chem. 2009, 19, 2975-2985.
12. a) J. Boutagy, R. Thomas, Chem. Rev. 1974, 74, 87-99;
13. b) W. S. Wadsworth, W. D. Emmons, J. Am. Chem. Soc. 1961, 83, 1733-1738.
14. Selected examples: a) B. A. Arbuzov, Pure Appl. Chem. 1964, 9, 315-370;
15. b) B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863-927;
16. c) S. A. Snyder, S. P. Breazzano, A. G. Ross, Y. Lin, A. L. Zografos, J. Am. Chem. Soc. 2009, 131, 1753-1765.
17. a) C. F. Stephen, Tetrahedron 1999, 55, 12237-12273;
18. b) R. J. Cohen, D. L. Fox, J. F. Eubank, R. N. Salvatore, Tetrahedron Lett. 2003, 44, 8617-8621.
19. a) E. Balaraman, V. Srinivas, K. C. Kumara Swamy, Tetrahedron 2009, 65, 7603-7610;
20. b) J. Kanada, K. Yamashita, S. K. Nune, M. Tanaka, Tetrahedron Lett. 2009, 50, 6196-6199;
21. c) V. P. Ananikov, L. L. Khemchyan, I. P. Beletskaya, Z. A. Starikova, Adv. Synth. Catal. 2010, 352, 2979-2992;
22. d) V. Srinivas, E. Balaraman, K. V. Sajna, K. C. Kumara Swamy, Eur. J. Org. Chem. 2011, 2011, 4222-4230;
23. e) Q. Xu, R. Shen, Y. Ono, R. Nagahata, S. Shimada, M. Goto, L. B. Han, Chem. Commun. 2011, 47, 2333-2335.
24. a) G. Lavén, J. Stawinski, Synlett 2009, 225-228;
25. b) G. Lavén, M. Kalek, M. Jezowska, J. Stawinski, New J. Chem. 2010, 34, 967-975;
26. c) G. G. Rajeshwaran, M. Nandakumar, R. Sureshbabu, A. K. Mohanakrishnan, Org. Lett. 2011, 13, 1270-1273;
27. d) R. J. Barney, R. M. Richardson, D. F. Wiemer, J. Org. Chem. 2011, 76, 2875-2879;
28. e) L. Rout, S. Regati, C. G. Zhao, Adv. Synth. Catal. 2011, 353, 3340-3346;
29. f) S. M. A. Kedrowski, D. A. Dougherty, Org. Lett. 2010, 12, 3990-3993.
30. a) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482-1485;
31. Angew. Chem. Int. Ed. 2001, 40, 1433-1436;
32. b) V. K. Aggarwal, E. Alonso, G. Hynd, K. M. Lydon, M. J. Palmer, M. Porcelloni, J. R. Studley, Angew. Chem. 2001, 113, 1479-1482;
33. Angew. Chem. Int. Ed. 2001, 40, 1430-1433;
34. c) V. K. Aggarwal, J. R. Fulton, C. G. Sheldon, J. de Vicente, J. Am. Chem. Soc. 2003, 125, 6034-6035;
35. d) K. Inamoto, T. Saito, M. Katsuno, T. Sakamoto, K. Hiroya, Org. Lett. 2007, 9, 2931-2934.
36. a) J. Barluenga, P. Moriel, C. Valdes, F. Aznar, Angew. Chem. 2007, 119, 5683-5686;
37. Angew. Chem. Int. Ed. 2007, 46, 5587-5590;
38. b) J. Barluenga, M. Tomás- Gamasa, F. Aznar, C. Valdés, Nat. Chem. 2009, 1, 494-499;
39. c) J. Barluenga, M. Escribano, F. Aznar, C. Valdés, Angew. Chem. 2010, 122, 7008-7011;
40. Angew. Chem. Int. Ed. 2010, 49, 6856-6859;
41. d) J. Barluenga, L. Florentino, F. Aznar, C. Valdes, Org. Lett. 2011, 13, 510-513;
42. e) J. Barluenga, M. Tomás-Gamasa, F. Aznar, C. Valdés, Angew. Chem. 2010, 122, 5113-5116;
43. Angew. Chem. Int. Ed. 2010, 49, 4993-4996;
44. f) J. Barluenga, N. Quinones, M. P. Cabal, F. Aznar, C. Valdes, Angew. Chem. 2011, 123, 2398-2401;
45. Angew. Chem. Int. Ed. 2011, 50, 2350-2353;
46. g) J. Barluenga, C. Valdes, Angew. Chem. 2011, 123, 7626-7640;
47. Angew. Chem. Int. Ed. 2011, 50, 7486-7500.
48. a) Q. Xiao, J. Ma, Y. Yang, Y. Zhang, J. B. Wang, Org. Lett. 2009, 11, 4732-4735;
49. b) L. Zhou, F. Ye, Y. Zhang, J. B. Wang, J. Am. Chem. Soc. 2010, 132, 13590-13591;
50. c) Q. Xiao, Y. Xia, H. A. Li, Y. Zhang, J. B. Wang, Angew. Chem. 2011, 123, 1146-1149;
51. Angew. Chem. Int. Ed. 2011, 50, 1114-1117;
52. d) L. Zhou, Y. Shi, Q. Xiao, Y. Z. Liu, F. Ye, Y. Zhang, J. B. Wang, Org. Lett. 2011, 13, 968-971;
53. e) L. Zhou, F. Ye, J. C. Ma, Y. Zhang, J. B. Wang, Angew. Chem. 2011, 123, 3572-3576;
54. Angew. Chem. Int. Ed. 2011, 50, 3510-3514.
55. S. H. Bertz, G. Dabbagh, J. Am. Chem. Soc. 1981, 103, 5932-5934.
56. S. Inokawa, Y. Nakatsukasa, M. Horisaki, M. Yamashita, H. Yoshida, T. Ogata, H. Inokawa, Synthesis 1977, 179-180.
57. M. Yamashita, J. Takeuchi, K. Nakatani, T. Oshikawa, S. Inokawa, Bull. Chem. Soc. Jpn. 1985, 58, 377-378.
58. a) Y. X. Gao, G. Wang, L. Chen, P. X. Xu, Y. F. Zhao, Y. B. Zhou, L. B. Han, J. Am. Chem. Soc. 2009, 131, 7956-7957;
59. b) R. Q. Zhuang, J. Xu, Z. S. Cai, G. Tang, M. J. Fang, Y. F. Zhao, Org. Lett. 2011, 13, 2110-2113;
60. c) C. Zhang, Z. Xu, L. Zhang, N. Jiao, Angew. Chem. 2011, 123, 11284-11288;
61. Angew. Chem. Int. Ed. 2011, 50, 11088-11092;
62. d) C. Zhang, C. Tang, N. Jiao, Chem. Soc Rev. 2012, 41, 3464-3484.
63. a) M. R. Crimmin, A. G. M. Barrett, M. S. Hill, P. B. Hitchcock, P. A. Procopiou, Organometallics 2007, 26, 2953-2956;
64. b) C. J. Xi, X. Y. Yan, C. B. Lai, K.-i. Kanno, T. Takahashi, Organometallics 2008, 27, 3834-3839;
65. c) H. Takahashi, S. Inagaki, N. Yoshii, F. Gao, Y. Nishihara, K. Takagi, J. Org. Chem. 2009, 74, 2794-2797;
66. d) M. Sun, H. Y. Zhang, Q. Han, K. Yang, S. D. Yang, Chem. Eur. J. 2011, 17, 9566-9570;
67. e) L. B. Han, F. Mirzaei, C. Q. Zhao, M. Tanaka, J. Am. Chem. Soc. 2000, 122, 5407-5408.
68. a) X. W. Feng, J. Wang, J. Zhang, J. Yang, N. Wang, X. Q. Yu, Org Lett. 2010, 12, 4408-4411;
69. b) S. F. Zhu, B. Xu, G. P. Wang, Q. L. Zhou, J. Am. Chem. Soc. 2012, 134, 436-442.