A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester

Chemistry - A European Journal

Volumn 12, Issue 13, 2006, Pages 3636-3646

  Rao, Honghua ^a   Jin, Ying ^a   Fu, Hua ^a   Jiang, Yuyang ^a   Zhao, Yufen ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

Arylation; Copper; Cross coupling; Homogeneous catalysis; N,O ligands

Indexed keywords

CATALYST ACTIVITY; CHEMICAL REACTIONS; COPPER; ESTERS;

ARYLATION; CROSS-COUPLING; HOMOGENEOUS CATALYSIS; N,O LIGANDS;

CHEMICAL BONDS;

CARBON; COPPER; LIGAND; NITROGEN; OXYGEN; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS; PYRROLIDINE 2 PHOSPHONIC ACID PHENYL MONOESTER; PYRROLIDINE DERIVATIVE; PYRROLIDINE-2-PHOSPHONIC ACID PHENYL MONOESTER;

ARTICLE; CATALYSIS; CHEMISTRY; METABOLISM; METHODOLOGY;

CARBON; CATALYSIS; CHEMISTRY; COPPER; LIGANDS; NITROGEN; OXYGEN; PHOSPHONIC ACIDS; PHOSPHORUS; PYRROLIDINES;

EID: 33646192747     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501473     Document Type: Article

References (118)

1. M. Negwer in Organic-Chemical Drugs and their Synonyms: (An International Survey), 7th ed., Akademie Verlag, Berlin, 1994.
2. a) D. A. Evans, K. M. DeVries in Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences, Vol. 63 (Ed.: R. Nagarajan), Marcel Decker, New York, 1994, pp. 63;
3. b) F. Theil, Angew. Chem. 1999, 111, 2493;
4. Angew. Chem. Int. Ed. 1999, 38, 2345;;
5. c) D. H. Williams, Acc. Chem. Res. 1984, 17, 364;
6. J. W. Janetka, P. Raman, K. Satyshur, G. R. Flentke, D. H. Rich, J. Am. Chem. Soc. 1997, 119, 441;
7. e) K. C. Nicolaou, C. N. C. Boddy, S. Natarajan, T.-Y. Yue, H. Li, S. Bräse, J. M. Ramanjulu, J. Am. Chem. Soc. 1997, 119, 3421;
8. f) D. L. Boger, M. A. Patane, J. Zhou, J. Am. Chem. Soc. 1994, 116, 8544.
9. For reviews, see: a) A. L. Schwan, Chem. Soc. Rev. 2004, 33, 218;
10. b) I. P. Beletskaya, M. A. Kazankova, Russ. J. Org. Chem. 2002, 38, 1391;
11. for other related studies, see: c) D. Cai, J. F. Payack, D. R. Bender, D. L. Hughes, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1994, 59, 7180;
12. d) J.-L. Montchamp, J. Organomet. Chem. 2005, 690, 2388;
13. e) I. P. Beletskaya, V. V. Afanasiev, M. A. Kazankova, I. V. Efimova, Org. Lett. 2003, 5, 4309.
14. For reviews, see: a) J. F. Hartwig, Angew. Chem. 1998, 110, 2154;
15. Angew. Chem. Int. Ed. 1998, 37, 2046;;
16. b) J. P. Wolfe, S. Wagaw, J.-F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805;
17. c) A. R. Muci, S. L. Buchwald, Topics in Current Chemistry, Vol. 219, Springer, Heidelberg, 2002, Chap. 5;
18. d) J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852.
19. Palladium-mediated ether synthesis: a) K. E. Torraca, X. Huang, C. A. Parrish, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 10770;
20. b) A. Aranyos, D. W. Old, A. Kiyomori, J. P. Wolfe, J. P. Sadighi, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4369;
21. c) G. Mann, C. Incarvito, A. L. Rheigold, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 3224
22. d) Q. Shelby, N. Kataoka, G. Mann, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 10718.
23. Palladium-catalyzed P-C bond formation: a) K. Bravo-Altamirano, Z. Huang, J.-L. Montchanmp, Tetrahedron 2005, 61, 6315;
24. b) H. Lei, M.S. Stoakes, A. W. Schwabacher, Synthesis 1992, 1255;
25. c) A. W. Schwabacher, S. Zhang, W. Davy, J. Am. Chem. Soc. 1993, 115, 6995.
26. For reviews, see: a) K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 15, 2428;
27. b) S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558;
28. Angew. Chem. Int. Ed. 2003, 42, 5400;;
29. c) I. P. Beletskaya, A. V. Cheprakov. Coord. Chem. Rev. 2004, 248, 2337;
30. for other related studies, see: d) K. Okano, H. Tokuyama, T. Fukuyama, Org. Lett. 2003, 5, 4987
31. e) C. Han, R. Shen, S. Su, J. A. Porco, Jr., Org. Lett. 2004, 6, 27;
32. f) E. Buck, Z. J. Song, D. Tschaen, P. G. Dormer, R. P. Volante, P. Reider, Org. Lett. 2002, 4, 1623.
33. Some recent reports: a) J.-F. Marcoux, S. Doye, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 10539;
34. b) E. Buck, Z. J. Song, D. Tschaen, P. G. Dormer, R. P. Volante, P. J. Reider, Org. Lett. 2002, 4, 1623;
35. c) C. Palomo, M. Oiarbide, R. Lopez, E. Gomez-Bengoa, Chem. Commun. 1998, 2091;
36. d) D. Ma, Q. Cai, Org. Lett. 2003, 5, 3799;
37. e) P. J. Fagan, E. Hauptman, R. Shapiro, A. Casalnuovo, J. Am. Chem. Soc. 2000, 122, 5043;
38. f) R. K. Gujadhur, C. G. Bates, D. Venkataraman, Org. Lett. 2001, 3, 4135;
39. g) H. J. Cristau, P. P. Cellier, S. Hamada, J. F. Spindler, M. Tailefer, Org. Lett. 2004, 6, 913.
40. a) R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, M. Alikarami, Synlett 2005, 1101;
41. b) M. Wolter, G. Nordmann, G. E. Job, S. L. Buchwald, Org. Lett. 2002, 4, 973;
42. c) A. Zapf, M. Beller, T. H. Riermeier in Transition Metals for Organic Synthesis, Vol. 1, 2nd ed. (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, p. 231.
43. a) A. Klapars, J. C. Antilla, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727;
44. b) J. C. Antilla, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 11684;
45. c) J. C. Antilla, J. M. Baskin, T. E. Barder, S. L. Bchwald, J. Org. Chem. 2004, 69, 5578.
46. a) R. K. Gujadhur, C. G. Bates, D. Venkataraman, Org. Lett. 2001, 3, 4315;
47. b) D. van Allen, D. Venkataraman, J. Org. Chem. 2003, 68, 4590.
48. a) F. Y. Kwong, A. Klapars, S. L. Buchwald, Org. Lett. 2002, 4, 581;
49. b) F. Y. Kwong, S. L. Buchwald, Org. Lett. 2003, 5, 793.
50. a) D. Ma, Y. Zhang, J. Yao, S. Wu, F. Tao, J. Am. Chem. Soc. 1998, 120, 12459;
51. b) D. Ma, C. Xia, Org. Lett. 2001, 3, 2583;
52. c) D. Ma, Q. Cai, H. Zhang, Org. Lett. 2003, 5, 2453;
53. d) D. Ma, Q. Cai, Org. Lett. 2003, 5, 3799;
54. e) D. Ma, Q. Cai, Synlett 2004, 1, 128;
55. f) X. Pan, Q. Cai, D. Ma, Org. Lett. 2004, 6, 1809;
56. g) W. Zhu, D. Ma, Chem. Commun. 2004, 888;
57. h) D. Ma, F. Liu, Chem. Commun. 2004, 1934;
58. i) H. Zhang, Q. Cai, D. Ma, J. Org. Chem. 2005, 70, 5164.
59. a) H.-J. Cristau, P. P. Cellier, J.-F. Spindler, M. Taillefer, Eur. J. Org. Chem. 2004, 695;
60. b) H.-J. Cristau, P.P. Cellier, J.-F. Spindler, M. Taillefer, Chem. Eur. J. 2004, 10, 5607.
61. S. Zhang, D. Zhang, L. S. Liebeskind, J. Org. Chem. 1997, 62, 2312.
62. A.A. Kelkar, N.M. Patil, R. V. Chaudhari, Tetrahedron Lett. 2002, 43, 7143.
63. A. S. Gajare, K. Toyota, M. Yoshifuji, F. Yoshifuji, Chem. Commun. 2004, 1994.
64. a) T. Ogawa, N. Usuki, N. Ono, J. Chem. Soc. Perkin Trans. 1 1998, 2953;
65. b) D. Gelman, L. Jiang, S. L. Buchwald, Org. Lett. 2003, 5, 2315;
66. c) D. Van Allen, D. Venkataraman, J. Org. Chem. 2003, 68, 4590.
67. a) Y. Nomura, K. Ogawa, Y. Takeuchi, S. Tomoda, Chem. Lett. 1977, 693;
68. b) B. Boduszek, J. Oleksyszyn, C.-M. Kam, J. Selzler, R. E. Smith, J. C. Powers, J. Med. Chem. 1994, 37, 3969;
69. c) D. S. Tawfik, Z. Eshhar, A. Bentolila, B. S. Green, Synthesis 1993, 10, 968.
70. a) A. Klapars, J. C. Antilla, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727;
71. b) Z. Wang, R. T. Skerlj, G. J. Bridger, Tetrahedron Lett. 1999, 40, 3543;
72. c) M. Woler, A. Klapars, S. L. Buchwald, Org. Lett. 2001, 3, 3803.
73. S. Cacchi, G. Fabrizi, A. Goggiamani, E. Licandro, S. Maiorana, D. Perdicchia, Org. Lett. 2005, 7, 1497.
74. D. Pralay, B. Basudeb, Synth. Commun. 2004, 34, 2177.
75. I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2001, 4411.
76. a) K. W. Anderson, M. Mendez-Perez, J. Priego, S. L. Buchwald, J. Org. Chem. 2003, 68, 9563;
77. b) J. Buckingham, S. M. Donaghy, Dictionary of Organic Compounds, Vol. 4, 5th ed., Chapman and Hall, New York, 1982, pp. 3943, 4244;
78. c) E. Brenner, R. Fort. Y. Schneider, Tetrahedron 1999, 55, 12829.
79. a) R. Kuwano, M. Utsunomiya, J. F. Hartwig, J. Org. Chem. 2002, 67, 6479;
80. b) Y. Tsuji, K. T. Huh, Y. Ohsugi, Y. Watanabe, J. Org. Chem. 1985, 50, 1365.
81. a) A. S. Gajare, K. Toyota, M. Yoshifuji, F. Ozawa, J. Org. Chem. 2004, 69, 6504;
82. b) S. Koichi, O. Toshiharu, O. Toshihiko, J. Am. Chem. Soc. 1981, 103, 645.
83. M. S. Wadia, D. V. Patil, Synth. Commun. 2003, 33, 2725.
84. G. Wullner, H. Jansch, S. Kauueuberg, F. Schubert, G. Boche, Chem. Commun. 1998, 15, 1509.
85. a) S. M. S. Chauhan, R. G. Singh, Synth. Commun. 2003, 33, 2899;
86. b) J. J. Kulagowski, C. W. Rees, Synthesis 1980, 215.
87. M. B. Floyd, M. T. Du, P. F. Fabio, L. A. Jacob, B. D. Johnson, J. Org. Chem. 1985, 50, 5022.
88. M.-H. Wu, G.-C. Yang, Z.-X. Chen, Chin. J. Chem. 2001, 19, 173.
89. B. S. Furniss, A. J. Hannaford, V. Rogers, P. W. G. Smith, A. R. Tatchell, Qualitative Organic Analysis; Physical Constants of Organic Compounds in Vogel's Textbook of Practical Organic Chemistry, 4th Ed., Longman, London & New York, 1978, Chaps. VII and VIII, pp. 1113, 1194, 1222.
90. B.-S. Koo, E.-H. Kim, K.-J. Lee, Synth. Commun. 2002, 32, 2275.
91. J. J. Yin, S. L. Buchwald, Org. Lett. 2000, 2, 1101.
92. T. Zhou, Z.-C. Chen, Synth. Commun. 2002, 32, 903.
93. J. P. Collman, M. Zhong, Org. Lett. 2000, 2, 1233.
94. L. Wang, Z.-C. Chen, J. Chem. Res. 2000, 8, 367.
95. G. Boche, R. H. Sommerlade, F. Bosold, Angew. Chem. 1986, 98, 563;
96. Angew. Chem. Int. Ed. Engl. 1986, 25, 562.
97. A. S. Shawali, H. M. Hassaneen, S. Almousawi, Bull. Chem. Soc. Jpn. 1978, 51, 512.
98. H. J. Cristau, P.P. Cellier, S. Hamada, J. F. Spindler, M. Tailefer, Org. Lett. 2004, 6, 913.
99. N. Haga, H. Takayanagi, J. Org. Chem. 1996, 61, 735.
100. D. H. R. Barton, N. Yadav-Bhatnagar, J.-P. Finet, J. Khamsi, W. B. Motherwell, S. P. Stanforth, Tetrahedron 1987, 43, 323.
101. A. Aranyos, D. W. Old, A. Kiyomori, J. P. Wolfe, J. P. Sadighi, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4369.
102. S. M. S. Chauhan, N. Jain, A. Kumar, K. A. Srinivas, Synth. Commun. 2003, 33, 3607.
103. R. Q. Brewster, G. Tevenson, J. Am. Chem. Soc. 1940, 62, 3144.
104. K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi, T. Horaguchiy, Chem. Lett. 2003, 32, 932.
105. J. Forrest, J. Chem. Soc. 1960, 581-588.
106. G. L. Rebeiro, B. M. Khadilkar, Synth. Commun. 2003, 33, 1405.
107. L. Fan, Y. Zhang, Y. Wang, J. Liu, M. Ma, S. Chen, Huaxue Yanjiu Yu Yingyong 2001, 13, 336.
108. A. J. Hill, W. J. McGraw, J. Org. Chem. 1949, 14, 783.
109. P. R. Ortiz de Montellano, L. A. Grab, Biochemistry 1987, 26, 5310.
110. C. K. Lai, Y.-S. Pang, C.-H. Tsai, J. Mater. Chem. 1998, 8, 2605.
111. J.-L. Montchamp, F. Tian, J. W. Frost, J. Org. Chem. 1995, 60, 6076.
112. T. Zhou, Z.-C. Chen, Synth. Commun. 2001, 31, 3289.
113. A. Kockritz, A. Weigt, M. Kant, Phosphorus Sulfur Silicon Relat. Elem. 1996, 117, 287.
114. C. Edder, J. M. J. Fréchet, Org. Lett. 2003, 5, 1879.
115. R. K. Bhardwaj, R. S. Davidson, Tetrahedron 1987, 43, 4473.
116. M. J. P. Harger, A. Smith, J. Chem. Soc. Perkin Trans. 1 1985, 1787.
117. J.-L. Montchamp, Y. R. Dumond, J. Am. Chem. Soc. 2001, 123, 510.
118. B. Boduszek, Synth. Commun. 2003, 33, 4087.