Syntheses of phosphine ligands via palladium-catalyzed P-C coupling reactions

Progress in Chemistry

Volumn 16, Issue 1, 2004, Pages 90-98

  Zhang, Tianzhu ^a   Xu, Lijin ^a   Sun, Wenhua ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

C C coupling; Chiral phosphines; P C coupling; Pd catalysis; Synthesis of phosphine compounds

Indexed keywords

PALLADIUM; PHOSPHINE DERIVATIVE;

CATALYSIS; CHEMICAL REACTION; CHIRALITY; METHODOLOGY; REVIEW; SYNTHESIS;

EID: 10844258894     PISSN: 1005281X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (107)

1. Tsuji J. Transition Metal Reagents and Catalysts-Innovations in Organic Synthesis. Chichester: Wiley, 2000
2. Li J J, Gribble G W. Palladium in Heterocyclic Chemistry. Amsterdam: Pergamon, 2000
3. Hirao T, Masunaga T, Ohshiro Y, et al. Tetrahedron Lett., 1980, 21: 3595-3598
4. Hirao T, Masunaga T, Yamada N, et al. Bull. Chem. Soc. Jpn., 1982, 55: 909-913
5. Xu Y, Li Z, Xia J, et al. Synthesis, 1983, 377-378
6. Xu Y, Zhang J. Synthesis 1984, 778-779
7. Xu Y, Li Z, Xia J, et al. Synthesis, 1984, 781-782
8. Xu Y, Xia J, Guo H. Synthesis 1986, 691-692
9. Xu Y, Zhang J. J. Chem. Soc. Chem. Commun., 1986, 1606
10. Zhang J, Xu Y, Huang G, et al. Tetrahedron Lett., 1988, 29: 1955-1958
11. Xu Y, Wei H, Zhang J, et al. Tetrahedron Lett., 1989, 30: 949-952
12. Tunney S E, Stille J K. J. Org. Chem., 1987, 52: 748-753
13. Imamoto T, Oshiki T, Onozawa T, et al. Heteratom. Chem., 1992, 3: 563-575
14. Oshiki T, Imamoto T. J. Am. Chem. Soc., 1992, 114: 3975-3976
15. Al-Masum M, Kumaraswamy G, Livinghouse T. J. Org. Chem., 2000, 65: 4776-4778
16. Al-Masum M, Livinghouse T. Tetrahedron Lett., 1999, 40: 7731-7734
17. Kurz L, Lee G, Morgans J D, et al. Tetrahedron Lett., 1990, 31: 6321-6324
18. Kwong F, Chan K. Organometallics, 2000, 19: 2058-2060
19. Kwong F, Chan K. Chem. Commun., 2000, 1069-1070
20. Kwong F, Lai C, Tian Y, et al. Tetrahedron Lett., 2000, 41: 10285-10289
21. Kwong F, Yang Q, Mak T C W, et al. J. Org. Chem., 2002, 67: 2769-2777
22. Iipshutz B H, Buzard D J, Yun C L. Tetrahedron Lett., 1999, 40: 201-204
23. Uozumi Y, Tanahashi A, Lee S, et al. J. Org. Chem., 1993, 58: 1945-1948
24. Uozumi Y, Suzuki N, Ogiwara A, et al. Tetrahedron, 1994, 50: 4293-4302
25. Hayashi T, Iwamura H, Uozumi Y, et al. Synthesis, 1994, 526-533
26. Hayashi T, Niizuma S, Kamikawa T, et al. J. Am. Chem. Soc., 1995, 117: 9101-9102
27. Ogasawara M, Yoshida K, Kamei H, et al. Tetrahedron: Asymmetry, 1998, 9: 1779-1787
28. Hayashi T, Hirate S, Kitayama K, et al. Chem. Lett., 2000, 1272-1273
29. Hayashi T, Hirate S, Kitayama K, et al. J. Org. Chem., 2001, 66: 1441-1449
30. Hayashi T, Ishigedani M. Tetrahedron, 2001, 57: 2589-2595
31. Hayashi T, Han J, Takeda A, et al. Adv. Synth. Catal., 2001, 343: 279-283
32. Han J, Hayashi T. Chem. Lett., 2001, 976-977
33. Han J, Hayashi T. Tetrahedron: Asymmetry, 2002, 13: 325-331
34. Hayashi T. Acta Chemica Scandinavica, 1996, 50: 259-266 and references therein.
35. Hayashi T J. Organomet. Chem., 1999, 576: 195-202 and references therein
36. Hayashi T. Catalysis Today, 2000, 62: 3-8 and references therein
37. Hayashi T. Acc. Chem. Res., 2000, 33: 354-362 and references therein
38. Hayashi T, Ishigedani M. J. Am. Chem. Soc., 2000, 122: 976-977
39. Ogasawara M, Yoshida K, Hayashi T. Heterocycles, 2000, 55: 195-201
40. Cavazzini M, Pozzi G, Quici S, et al. Chem. Commun., 2001, 1220-1221
41. Hamada T, Chieffi A, Ahman J, et al. J. Am. Chem. Soc., 2001, 123: 976-977
42. Sakai N, Mano S, Nozaki K, Takaya H. J. Am. Chem. Soc., 1993, 115: 7033-7034
43. Sakai N, Nozaki K, Takaya H. J. Chem. Soc. Chem. Commun., 1994, 395-396
44. Higashizima T, Sakai N, Nozaki K, et al. Tetrahedron Lett., 1994, 35: 2023-2026
45. Nozaki K, Sato N, Takaya H. J. Am. Chem. Soc., 1995, 117: 9911-9912
46. Horiuchi T, Ohta T, Shirakawa E, et al. J. Org. Chem., 1997, 62: 4285-4292
47. Nozaki K, Sakai N, Nanno T, et al. J. Am. Chem. Soc., 1997, 119: 4413-4423
48. Nozaki K, Takaya H, Hiyama T. Top. Catal., 1997, 4: 175-185
49. Nozaki K, Sato N, Tonomura Y, et al. J. Am. Chem. Soc., 1997, 119: 12779-12795
50. Nozaki K, Itoi Y, Shibahara F, et al. J. Am. Chem. Soc., 1998, 120: 4051-4052
51. Nozaki K, Shibahara F, Itoi Y, et al. Bull. Chem. Soc. Jpn., 1999, 72: 1911-1918
52. Nozaki K, Shibahara F, Stephan E, et al. J. Chem., 2001, 79: 593-597
53. Nozaki K, Matsuo T, Shibahara F, et al. Adv. Synth. Catal., 2001, 343: 61-63
54. Kainz S, Leitner W. Catal. Lett., 1998, 55: 223-225
55. Francio G, Leitner W. Chem. Commun., 1999, 1663-1664
56. Francio G, Wittmann K, Leitner W. J. Organomet. Chem., 2001, 621: 130-142
57. Horiuchi T, Ohta T, Stephan M, et al. Tetrahedron: Asymmetry, 1994, 5: 325-328
58. Lustenberger P, Diederich F. Helvetica Chim. Acta, 2000, 83: 2865-2883
59. Inagaki K, Ohta T, Nozaki K, et al. J. Organomet. Chem., 1997, 531: 159-163
60. Gladiali S, Dore A, Fabbrt D. Tetrahedron: Asymmetry, 1994, 5: 1143-1146
61. Gladiali S, Pulacchini S, Fabbri D, et al. Tetrahedron: Asymmetry, 1998, 9: 391-395
62. Gladiali S, Dore A, Fabbri D, et al. Eur. J. Org. Chem., 2000, 2861-2865
63. Cho S Y, Shibasaki M. Tetrahedron Lett., 1998, 39: 1773-1776
64. Kumobayashi H, Miura T, Sayo N, et al. Synlett, 2001, No. SI: 1055-1064
65. Vsykocil S, Smrcina M, Hanus V, et al. J. Org. Chem., 1998, 63: 7738-7748
66. Ding K, Wang Y, Yun H, et al. Chem. Eur. J., 1999, 5: 1734-1737
67. Wang Y, Guo H, Ding K. Tetrahedron: Asymmetry, 2000, 11: 4153-4162
68. Wang Y, Li X, Ding K. Tetrahedron Lett., 2002, 43: 159-161
69. Hu X, Chen H, Zhang X. Angew. Chem. Int. Ed., 1999, 38: 3518-3521
70. Hu X, Chen H, Zhang X. Acta Chimica Sinica, 2000, 58: 1156-1162
71. Hamada T, Buchwald S L. Org. Lett., 2002, 4: 999-1001
72. Alcock N W, Brown J M, Hulmes D I. Tetrahedron: Asymmetry, 1993, 4: 743-756
73. Brown J M, Hulmes D I, Layzell T P. J. Chem. Soc. Chem. Commun., 1993, 1673-1674
74. Valk J M, Whitlock G A, Layzell T P, Brown J M. Tetrahedron: Asymmetry, 1995, 6: 2593-2596
75. Valk J M, Claridge T D W, Brown J M. Tetrahedron: Asymmetry, 1995, 6: 2597-2610
76. Claridge T D W, Long J M, Brown J M, et al. Tetrahedron, 1997, 53: 4035-4050
77. Doucet H, Brown J M. Tetrahedron: Asymmetry, 1997, 8: 3775-3784
78. Doucet H, Fernandez E, Layzell T P, et al. Chem. Eur. J., 1999, 5: 1320-1330
79. Maeda K, Brown J M. Chem. Commun., 2002, 310-311
80. Chapoulaud V G, Ple J A N, Turck A, et al. Tetrahedron Lett., 1999, 40: 9005-9007
81. Ito K, Kashiwagi R, Iwasaki K, et al. Synlett, 1999, 1563-1566
82. Herd O, Heßler A, Hingst M, et al. J. Organomet. Chem., 1996, 522: 69-76
83. Herd O, Heßler A, Hingst M, et al. Catalysis Today, 1998, 42: 413-420
84. Machnitzki P, Nickel T, Stelzer O, et al. Eur. J. Inorg. Chem., 1998, 1029-1034
85. Machnitzki P, Tepper M, Wenz K, et al. J. Organomet. Chem., 2000, 602: 158-169
86. Brauer D J, Hingst M, Kottsieper K W, et al. J. Organomet. Chem., 2002, 645: 14-26
87. Bergbreiter D, Liu Y, Furyk S, et al. Tetrahedron Lett., 1998, 39: 8799-8802
88. Beller B, Krauter J G E, Zapf A, et al. Catalysis Today, 1999, 48: 279-290
89. Beller M, Fischer H, Herrmann W A, et al. Angew. Chem. Int. Ed. Engl., 1995, 34: 1848-1849
90. Jiang J, Wang Y, Liu C, et al. J. Mol. Catal. A: Chem., 2001, 171: 85-89
91. Gilbertson S R, Starkey G W. J. Org. Chem., 1996, 61: 2922-2923
92. Gilbertson S R, Fu Z, Starkey G W. Tetrahedron Lett., 1999, 40: 8509-8512
93. Gilbertson S R, Fu Z. Org. Lett., 2001, 3: 161-164
94. Martorell G, Garcias X, Janura M, et al. J. Org. Chem., 1998, 63: 3463-3467
95. Skoda-Foldes R, Banffy L, Horvath J, et al. Monatshefte fur Chemie, 2000, 131: 1363-1369
96. Kanbara T, Takase S, Izumi K, et al. Macromolecules, 2000, 33: 657-659
97. Fujie N, Matsui M, Achiwa K. Chem. Pharm. Bull., 1999, 47: 436-439
98. Nandi M, Jin J, Rajanbabu T V. J. Am. Chem. Soc., 1999, 121: 9899-9900
99. Yan Y, Rajanbabu T V. J. Org. Chem., 2000, 65: 900-906
100. Kazankova M A, Efimova I V, Kochetkov A N, et al. Synlett, 2001, 497-500
101. Allen A, Ma L, Lin W. Tetrahedron Lett., 2002, 43: 3707-3710
102. Trost B M, Marschner C. Bull. Soc. Chim. Fr., 1997, 134: 263-274
103. Trost B M, Radinov R. J. Am. Chem. Soc., 1997, 119: 5962-5963
104. Trost B M, Bunt R C, Lemoine R C, et al. J. Am. Chem. Soc., 2000, 122: 5968-5976
105. Chen W, Xu L, Xiao J. Org. Lett., 2000, 2: 2675-2677
106. Hu Y, Chen W, Xu L, et al. Organometallics, 2001, 14: 3206-3208
107. Baillie C, Chen W, Xiao J. Tetrahedron Lett., 2001, 42: 9085-9088