Recent developments on hemilabile P,O-type ligands in cross-coupling reactions

Synlett

Volumn , Issue 10, 2008, Pages 1440-1448

  Kwong, Fuk Yee ^a   Chan, Albert S C ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Catalysis; Cross coupling; Ligands; P,O co ordination; Phosphines

Indexed keywords

ACETAL DERIVATIVE; AMIDE; FERROCENE DERIVATIVE; LIGAND; PHOSPHINE DERIVATIVE; SULFONE DERIVATIVE; TRANSITION ELEMENT;

AMINATION; CATALYSIS; CATALYST; CHIRALITY; COMPLEX FORMATION; CROSS COUPLING REACTION; ENANTIOSELECTIVITY; HECK REACTION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; REVIEW; STEREOSPECIFICITY; SYNTHESIS;

EID: 46449092042     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/S-2008-1078425     Document Type: Review

References (79)

1. Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis: Targets, Strategies, and Methods; VCH: Weinheim, 1996.
2. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
3. Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
4. For recent reviews on C-C bond formations, see: (a) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
5. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
6. For recent reviews on C-X bond formations, see: (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
7. (b) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000.
8. (a) Handbook of Organopalladium Chemistry for Organic Synthesis, Vols. 1-2; Negishi, E.-I., Ed.; Wiley-Interscience: New York, 2002.
9. (b) Perspectives in Organopalladium Chemistry for the XXI Century; Tsuji, J., Ed.; Elsevier: Amsterdam, 1999.
10. (c) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
11. (d) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; John Wiley & Sons: Weinheim, 2004.
12. For selected references, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem. Int. Ed. 2000, 39, 4153.
13. (b) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209.
14. (c) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38.
15. (d) Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Riermeier, T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem. Eur. J. 2004, 10, 2983.
16. (e) Sergeev, A. G.; Zapf, A.; Spannenberg, A.; Beller, M. Organometallics 2008, 27, 297.
17. For selected references, see: (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
18. (b) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
19. (c) Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818.
20. (d) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2004, 43, 1871.
21. (e) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
22. (f) Biscoe, M. R.; Barder, T. E.; Buchwald, S. L. Angew. Chem. Int. Ed. 2007, 46, 7232.
23. (g) Barder, T. E.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 12003.
24. (h) Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358.
25. For selected references, see: (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
26. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408.
27. (c) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
28. For selected references, see: (a) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
29. (b) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem. Int. Ed. 2002, 41, 4746.
30. (c) Hama, T.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 4976.
31. (d) Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 10028.
32. (e) Fernandez-Rodriguez, M. A.; Shen, Q.; Hartwig, J. F. Chem. Eur. J. 2006, 12, 7782.
33. (f) Shekhar, S.; Hartwig, J. F. Organometallics 2007, 26, 340.
34. (g) Vo, G. D.; Hartwig, J. F. Angew. Chem. Int. Ed. 2008, 47, 2127.
35. For selected references, see: (a) Li, G. Y. Angew. Chem. Int. Ed. 2001, 40, 1513.
36. (b) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
37. (c) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
38. (d) Colacot, T. J.; Shea, H. A. Org. Lett. 2004, 6, 3731.
39. (e) Brenstrum, T.; Clattenburg, J.; Britten, J.; Zavorine, S.; Dyckx, J.; Robertson, A. J.; McNulty, J.; Capretta, A. Org. Lett. 2006, 8, 103.
40. (f) So, C. M.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2007, 9, 2795.
41. (g) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840.
42. (h) Feuerstein, M.; Berthiol, F.; Doucet, H.; Santelli, M. Synlett 2002, 1807.
43. (i) Gstottmayr, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363.
44. (j) Kwong, F. Y.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. Commun. 2004, 2336.
45. (k) Dai, Q.; Gao, W.; Liu, D.; Kapes, L. M.; Zhang, X. J. Org. Chem. 2006, 71, 3928.
46. (l) Grasa, G. A.; Colacot, T. J. Org. Lett. 2007, 9, 5489.
47. (m) Reddy, Ch. V.; Kingston, J. V.; Verkade, J. G. J. Org. Chem. 2008, 73, 3047.
48. (a) Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27.
49. (b) Espinet, P.; Soulantica, K. Coord. Chem. Rev. 1999, 193-195, 499.
50. Molina, P.; Arques, A.; Garca, A.; Ramirez de Arellano, M. C. Eur. J. Inorg. Chem. 1998, 1359; and references cited therein.
51. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
52. Amatore, A.; Fuxa, A.; Jutand, A. Chem. Eur. J. 2000, 6, 1474.
53. Braunstein, P.; Naud, F. Angew. Chem. Int. Ed. 2001, 40, 680.
54. Bei, X.; Crevier, T.; Guram, A. S.; Jandeleit, B.; Powers, T. S.; Turner, H. W.; Uno, T.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855.
55. Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Peterson, J. L. J. Org. Chem. 1999, 64, 6797.
56. Bei, X.; Guram, A. S.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 1237.
57. Singer, R. A.; Tom, N. J.; Frost, H. N.; Simon, W. M. Tetrahedron Lett. 2004, 45, 4715.
58. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793.
59. Kwong, F. Y.; Lam, W. H.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. Commun. 2004, 1922.
60. (a) Dai, W.-M.; Li, Y.; Zhang, Y.; Lai, K. W.; Wu, J. Tetrahedron Lett. 2004, 45, 1999.
61. (b) Dai, W.-M.; Zhang, Y. Tetrahedron Lett. 2005, 46, 1377.
62. (a) Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem. Int. Ed. 2004, 43, 2206.
63. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
64. (c) Clayden, J. Tetrahedron Organic Chemistry Series - Organolithiums: Selectivity for Synthesis, Vol. 23; Pergamon: Oxford, 2002.
65. (a) Trost, B. M. Science 1991, 254, 1471.
66. (b) Trost, B. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 259.
67. 31P NMR spectroscopy showed no detectable phosphine oxide signal after storage for one month under air.
68. Chen, G.; Lam, W. H.; Fok, W. S.; Lee, H. W.; Kwong, F. Y. Chem. Asian J. 2007, 2, 306.
69. Kwong, F. Y.; Chan, A. S. C. unpublished results.
70. For a recent review on chiral ferrocenyl ligands, see: Colacot, T. J. Chem. Rev. 2003, 103, 3101.
71. Dai, W. M.; Yeung, K. K. Y.; Wang, Y. Tetrahedron 2004, 60, 4425.
72. Kwong, F. Y.; Choi, C. F.; Chen, G.; Chan, A. S. C. unpublished results.
73. For a recent reference on the asymmetric α-arylation of ketone enolates using Difluorphos, see: Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195.
74. Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153.
75. (a) Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 36, 6359.
76. (b) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
77. Josen, J. F.; Johannsen, M. Org. Lett. 2003, 5, 3025.
78. Atkinson, R. C. J.; Gibson, V. C.; Long, N. J.; White, A. J. P.; Williams, D. J. Organometallics 2004, 23, 2744.
79. Teo, S.; Weng, Z.; Hor, T. S. A. Organometallics 2006, 25, 1199.