Generation of an aromatic amide-derived phosphane (Aphos) library by self-assisted molecular editing and applications of Aphos in room-temperature Suzuki-Miyaura reactions

Chemistry - A European Journal

Volumn 14, Issue 18, 2008, Pages 5538-5554

  Dai, Wei Min ^a,b   Li, Yannian ^a,b   Zhang, Ye ^b   Yue, Congyong ^a,b   Wu, Jinlong ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Heterogeneous catalysis; Microwave assisted reactions; Palladium; Phosphanes; Suzuki Miyaura coupling

Indexed keywords

ACIDS; AMIDES; AROMATIC COMPOUNDS; COMPLEXATION; MICROWAVE IRRADIATION; MICROWAVES; NETWORK PROTOCOLS; PALLADIUM; STRUCTURAL DESIGN; STRUCTURAL OPTIMIZATION;

HETEROGENEOUS CATALYSIS; MICROWAVE-ASSISTED REACTIONS; PHOSPHANES; SUZUKI-MIYAURA COUPLING;

LIGANDS;

EID: 53949086521     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800318     Document Type: Article

References (144)

1. N. Miyaura, K. Yamade, A. Suzuki, Tetrahedron Lett. 1979, 20, 3437-3440.
2. For reviews, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
3. b) S. P. Stanforth, Tetrahedron 1998, 54, 263-303;
4. c) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633-9695;
5. d) J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469;
6. e) F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 2419-2440;
7. f) N. T. S. Phan, M. V. D. Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609-679.
8. a) T. Ishiyama, S. Abe, N. Miyaura, A. Suzuki, Chem. Lett. 1992, 691-694;
9. b) M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100;
10. c) J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027;
11. Angew. Chem. Int. Ed. 2002, 41, 1945-1947;
12. d) M. R. Netherton, G. C. Fu, Angew. Chem. 2002, 114, 4066-4068;
13. Angew. Chem. Int. Ed. 2002, 41, 3910-3912;
14. e) J. H. Kirchhoff, M. R. Netherton, I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 13662-13663;
15. f) I. D. Hills, M. R. Netherton, G. C. Fu, Angew. Chem. 2003, 115, 5927-5930;
16. Angew. Chem. Int. Ed. 2003, 42, 5749-5752;
17. g) K. Arentsen, S. Caddick, F. G. N. Coke, A. P. Herring, P. B. Hitchcock, Tetrahedron Lett. 2004, 45, 3511-3515.
18. For a review, see: A. C. Frisch, M. Beller, Angew. Chem. 2005, 117, 680-695;
19. Angew. Chem. Int. Ed. 2005, 44, 674-688.
20. For reviews, see: a) A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386;
21. Angew. Chem. Int. Ed. 2002, 41, 4176-4211;
22. b) R. B. Bedford, C. S. J. Cazin, D. Holder, Coord. Chem. Rev. 2004, 248, 2283-2321.
23. a) M. Miura, Angew. Chem. 2004, 116, 2251-2253;
24. Angew. Chem. Int. Ed. 2004, 43, 2201-2203;
25. b) U. Christmann, R. Vilar, Angew. Chem. 2005, 117, 370-378;
26. Angew. Chem. Int. Ed. 2005, 44, 366-374.
27. 3 in carbonylation of aryl chlorides, see:
28. b) M. Huser, M. T. Youinou, J. A. Osborn, Angew. Chem. 1989, 101, 1427-1430;
29. Angew. Chem. Int. Ed. Engl. 1989, 28, 1386-1388;
30. c) V. V. Grushin, H. Alper, J. Chem. Soc. Chem. Commun. 1992, 611-612.
31. a) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587;
32. Angew. Chem. Int. Ed. 1998, 37, 3387-3388;
33. 4, see:
34. 2]
35. see: d) J. P. Slambuli, R. Kuwano, J. F. Hartwig, Angew. Chem. 2002, 114, 4940-4942;
36. Angew. Chem. Int. Ed. 2002, 41, 4746-4748.
37. a) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723;
38. b) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561;
39. c) J. P. Wolfe, S. L. Buchwald. Angew. Chem. 1999, 111, 2570-2573;
40. Angew. Chem. Int. Ed. 1999, 38, 2413-2416;
41. d) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907-1912;
42. Angew. Chem. Int. Ed. 2004, 43, 1871-1876;
43. e) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696;
44. f) K. W. Anderson, S. L. Buchwald, Angew. Chem. 2005, 117, 6329-6333;
45. Angew. Chem. Int. Ed. 2005, 44, 6173-6177.
46. W.-M. Dai, Y. Zhang, Tetrahedron Lett. 2005, 46, 1377-1381.
47. For 4-substituted phenyl di-tert-butylphosphanes, see: a) A. S. Guram, A. O. King, J. G. Allen, X. Wang, L. B. Schenkel, J. Chan, E. E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, P. J. Reider, Org. Lett. 2006, 8, 1787-1789; for phosphino substituted N-aryl pyrroles, see:
48. b) A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh, U. Dingerdissen, M. Beller, Chem. Commun. 2004, 38-39; for bulky trialkylphosphanes, see:
49. c) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317;
50. Angew. Chem. Int. Ed. 2000, 39, 4153-4155; for ferrocene-derived Q-phos, see:
51. d) N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig. J. Org. Chem. 2002, 67, 5553-5566.
52. W. A. Herrmann, C.-P Reisinger, M. Spiegler, J. Organomet. Chem. 1998, 557, 93-96.
53. For reviews, see: a) W. A. Herrmann, Angew. Chem. 2002, 114, 1342-1363;
54. Angew. Chem. Int. Ed. 2002, 41, 1290-1309;
55. b) S. Díez-González, S. P. Nolan, Coord. Chem. Rev. 2007, 251, 874-883;
56. c) E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 120, 2824-2870;
57. Angew. Chem. Int. Ed. 2007, 46, 2768-2813.
58. C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M Grosche, W. A. Herrmann, Angew. Chem. 2002, 114, 1421-1423;
59. Angew. Chem. Int. Ed. 2002, 41, 1363-1365.
60. a) O. Navarro, R. A. Kelly, III, S. P. Nolan, J. Am. Chem. Soc. 2003, 125, 16194-16195;
61. b) R. Singh, M. S. Viciu, N. Kramareva, O. Navarro, S. P. Nolan, Org. Lett. 2005, 7, 1829-1832;
62. c) O. Navarro, N. Marion, J. Mei, S. P. Nolan, Chem. Eur. J. 2006, 12, 5142-5148.
63. a) G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818-3821;
64. Angew. Chem. Int. Ed. 2003, 42, 3690-3693;
65. b) G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, J. Am. Chem. Soc. 2004, 126, 15195-15201.
66. C. Song, Y. Ma, Q. Chai, C. Ma, W. Jiang, M. B. Andrus, Tetrahedron 2005, 61, 7438-7446.
67. C. J. O'Brien, E. A. B. Kantchev, C. Valente, N. Hadei, G. A. Chass, A. Lough, A. C. Hopkinson, M. G. Organ, Chem. Eur. J. 2006, 12, 4743-4748.
68. For reviews, see: a) P. Braunstein, F. Naud. Angew. Chem. 2001, 113, 702-722;
69. Angew. Chem. Int. Ed. 2001, 40, 680-699;
70. b) Z. Weng, S. Teo, T. S. A. Hor, Acc. Chem. Res. 2001, 40, 676-684.
71. a) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858;
72. b) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. L. Petersen, J. Org. Chem. 1999, 64, 6797-6803.
73. a) W.-M. Dai, Y. Zhang, Abstr. Pap. 3rd Int. Sym. Chi. Med. Chemists (Hong Kong SAR, P. R. China) 2002, p. 127;
74. b) W.-M. Dai, Y. Li, Y. Zhang, K. W. Lai, J. Wu, Tetrahedron Lett. 2004, 45, 1999-2001; a diethylbenzamide analogue of our Aphos ligands was reported, see:
75. c) F. Y. Kwong, W. H. Lam, C. H. Yeung, K. S. Chan, A. S. C. Chan, Chem. Commun. 2004, 1922-1923.
76. a) J. Clayden, P. Johnson, J. H. Pink, M. Helliwell, J. Org. Chem. 2000, 65, 7033-7040;
77. b) J. Clayden, L. W. Lai, M. Helliwell, Tetrahedron 2001, 57, 695-698.
78. a) W.-M. Dai, K. K. Y. Yueng, J.-T. Liu, Y. Zhang, I. D. Williams, Org. Lett. 2002, 4, 1615-1618;
79. b) W.-M. Dai, K. K. Y. Yueng, Y. Wang, Tetrahedron 2004, 60, 4425-4430;
80. c) Y. Zhang, PhD thesis, The Hong Kong University of Science and Technology (P. R. China), 2005.
81. C. J. Chapman, C. G. Frost, M. F. Mahon, Dalton Trans. 2006, 2251-2262.
82. Some of the results were presented at a conference, see: W.-M. Dai, Abstr. Pap. Singapore Int. Chem. Conf. 4 (SICC-4) (Singapore) 2005, p. 77.
83. a) V. Snieckus, Chem. Rev. 1990, 90, 879-933;
84. b) M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256-2276;
85. Angew. Chem. Int. Ed. 2004, 43, 2206-2225.
86. a) C. P. Butts, J. Crosby, G. C. Lloyd-Jones, S. C. Stephen, Chem. Commun. 1999, 1707-1708;
87. b) Y. K. Kim, S. J. Lee, K. H. Ahn, J. Org. Chem. 2000, 65, 7807-7813;
88. c) G. Sánchez, J. García, D. Meseguer, J. L. Serano, L. García, J. Pérez, G. López, Dalton Trans. 2003, 4709-4717;
89. d) G. Sánchez, J. García, D. Meseguer, J. L. Serano, L. García, J. Pérez, G. López, Inorg. Chim. Acta 2006, 359, 1650-1658;
90. e) M. Lamač, I. Císařová, P. Štěpnička, Eur. J. Inorg. Chem. 2007, 2274-2287. For a Ru complex, see:
91. f) G. Sánchez, J. García, J. J. Ayllón, J. L. Serrano, L. García, J. Pérez, G. López, Polyhedron 2007, 26, 2911-2918.
92. K. K. Y. Yeung, Ph.D. thesis, The Hong Kong University of Science and Technology (P. R. China), 2003.
93. W.-M. Dai, C. W. Lau, Tetrahedron Lett. 2001, 42, 2541-2544.
94. a) P. Beak, R. A. Brown, J. Org. Chem. 1982, 47, 34-46;
95. b) R. J. Mills, N. J. Taylor, V. Snieckus, J. Org. Chem. 1989, 54, 4372-4385;
96. c) P. A. Brough, S. Fisher, B. Zhao, R. C. Thomas, V. Snieckus, Tetrahedron Lett. 1996, 37, 2915-2918.
97. a) G. Bazsa, M. T. Beck, Acta Chim. Acad. Sci. Hung. 1972, 73, 425-441;
98. b) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127;
99. Angew. Chem. Int. Ed. 1998, 37, 2922-2959;
100. c) M. H. Todd, Chem. Soc. Rev. 2002, 31, 211-222;
101. d) K. Mikami, M. Yamanak, Chem. Rev. 2003, 103, 3369-3400.
102. a) H. Krawczyk, Synlett 1998, 1114-1116;
103. b) E. Rochlin, Z. Rappoport, J. Org. Chem. 2003, 68, 1715-1720;
104. c) S. H. DuVall, R. L. McCreery, J. Am. Chem. Soc. 2000, 122, 6759-6764;
105. d) K. Broo, L. Brive, A.-C. Lundh, P. Ahlberg, L. Baltzer, J. Am. Chem. Soc. 1996, 118, 8172-8173;
106. e) E. L. Clennan, P. Dobrowolski, A. Greer, J. Am. Chem. Soc. 1995, 117, 9800-9803.
107. a) A. Robertson, A. J. Sinclair, D. Philp, Chem. Soc. Rev. 2000, 29, 141-152;
108. b) L. E. Orgel, Nature 1992, 358, 203-209;
109. c) E. Szalhmáry, Phil. Trans. R. Soc. Lond. B 2000, 355, 1669-1676.
110. The term self-assisted molecular evolution, has been used before, see refs. [23c] and [25]. It seems appropriate to use self-assisted molecular editing for the process described in this work.
111. M. D. Burke, S. L. Schreiber, Angew. Chem. 2004, 116, 48-60;
112. Angew. Chem. Int. Ed. 2004, 43, 46-58.
113. For selected reviews on microwave-assisted organic synthesis, see: a) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283;
114. b) M. Nüchter, B. Ondruschka, W. Bonrath, A. Gum, Green Chem. 2004, 6, 128-141;
115. c) C. O. Kappe, Angew. Chem. 2004, 116, 6408-6443;
116. Angew. Chem. Int. Ed. 2004, 43, 6250-6284;
117. d) A. de la Hoz, Á. Díaz-Ortiz, A. Moreno, Chem. Soc. Rev. 2005, 34, 164-178. Also see:
118. e) C O. Kappe, A. Stadler, Microwaves in Organic and Medicinal Chemistry, Wiley-VCH, Weinheim, 2005;
119. f) Micorwaves in Organic Synthesis, Vols. I and 2 (Ed.: A. Loupy), Wiley-VCH, Weinheim, 2006.
120. For leading references on Suzuki-Miyaura cross-coupling under controlled microwave heating, see: a) I. R. Baxendale, C. M. Griffiths-Jones, S. V. Ley, G. K. Tranmer, Chem. Eur. J. 2006, 12, 4407-4416;
121. b) R. K. Arvela, N. E. Leadbeater, Org. Lett. 2005, 7, 2101-2104;
122. c) N. E. Leadbeater, Chem. Commun. 2005, 2881-2902.
123. 31P signals listed in Table 1 were assigned to the newly formed C4-Ar-Cy-Aphos and 21 (plus the unreacted 17a in entry 19).
124. The slightly decreased efficiency (1 %) of 18c relative to 21 in the Suzuki-Miyaura coupling of 22 with phenylboronic acid may be taken as an experimental error.
125. a) C. Amatore, A. Jutand, A. Thuilliez, J. Organomet. Chem. 2002, 643-644, 416-423;
126. b) R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Orgnometallics 2003, 22, 987-999.
127. J. Jin, Y. Chen, Y. Li, J. Wu, W.-M. Dai, Org. Lett. 2007, 9, 2585-2588.
128. S. Teo, Z. Weng, T. S. A. Hor, Organometallics 2006, 25, 1199-1205.
129. For asymmetric Suzuki-Miyaura couplings, see: a) S. Y. Cho, M. Shibasaki, Tetrahedron: Asymmetry 1998, 9, 3751-3754;
130. b) K. C. Nicolaou, H. Li, C. N. C. Boddy, J. M. Ramanjulu, T.-Y. Yue, S. Natarajan, X.-J. Chu, S. Bräse, F. Rübsam, Chem. Eur. J. 1999, 5, 2584-2601;
131. c) A. N. Cammidge, K. V. L. Crépy, Chem. Commun. 2000, 1723-1724;
132. d) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051-12052;
133. e) A.-S. Castanet, F. Colobert, P.-E. Broutin, M. Obringer, Tetrahedron: Asymmetry 2002, 13, 659-665;
134. f) G. Bringmann, A. Hamm, M. Schraut, Org. Lett. 2003, 5, 2805-2808;
135. g) J. F. Jensen, M. Johannsen, Org. Lett. 2003, 5, 3025-3028;
136. h) A. Herrbach, A. Marinetti, O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem. 2003, 68, 4897-4905;
137. i) M. C. Willis, L. H. W. Powell, C. K. Claverie, S. J. Watson, Angew. Chem. 2004, 116, 1269-1271;
138. Angew. Chem. Int. Ed. 2004, 43, 1249-1251;
139. j) K. Mikami, T. Miyamoto, M. Halano, Chem. Commun. 2004, 2082-2083;
140. k) A. N. Cammidge, K. V. L. Crépy, Tetrahedron 2004, 60, 4377-4386;
141. l) M. Genov, A. Almorín, P. Espinel, Chem. Eur. J. 2006, 12, 9346-9352;
142. m) R. P. J. Bronger, P. J. Guiry, Tetrahedron: Asymmetry 2007, 18, 1094-1102.
143. M. T. Reelz, K. Sommer, Eur. J. Org. Chem. 2003, 18, 3485-3496.
144. T. Brenstrum, D. A. Gerristma, G. M. Adjabeng, C. S. Frampton, J. Britten, A. J. Robertson, J. McNulty, A. Capretta, J. Org. Chem. 2004, 69, 7635-7639.