Palladium-catalyzed phosphorus-carbon bond formation: Cross-coupling reactions of alkyl phosphinates with aryl, heteroaryl, alkenyl, benzylic, and allylic halides and triflates

Tetrahedron

Volumn 61, Issue 26, 2005, Pages 6315-6329

  Bravo Altamirano, Karla ^a   Huang, Zhihong ^a   Montchamp, Jean Luc ^a  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

Alkoxysilane; Cross coupling; Hypophosphorous; Palladium

Indexed keywords

CARBON; HALIDE; PALLADIUM; PHOSPHINE DERIVATIVE; PHOSPHORUS; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CROSS COUPLING REACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 20444436468     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.107     Document Type: Article

References (84)

1. Reviews: (a) J.F. Hartwig Acc. Chem. Res. 31 1998 852
2. D. Barañano, G. Mann, and J.F. Hartwig Curr. Org. Chem. 1 1997 287
3. See also references cited in: (c) M.C. Harris, and S.L. Buchwald J. Org. Chem. 65 2000 5327
4. J. Huang, G. Grasa, and S.P. Nolan Org. Lett. 1 1999 1307
5. M. Al-Masum, G. Kumaraswamy, and T. Livinghouse J. Org. Chem. 65 2000 4776
6. T. Oshidi, and T. Imamoto J. Am. Chem. Soc. 114 1992 3975
7. For examples of transition metal catalyzed P-C bond formation via cross-coupling: (a) G. Martorell, X. Garcías, M. Janura, and J.M. Saá J. Org. Chem. 63 1998 3463
8. R.J. Hinkle, P.J. Stang, and M.H. Kowalski J. Org. Chem. 55 1990 5033
9. S.E. Tunney, and J.K. Stille J. Org. Chem. 52 1987 748
10. Y. Xu, and J. Zhang Synthesis 1984 778
11. Y. Xu, Z. Li, J. Xia, H. Guo, and Y. Huang Synthesis 1983 377
12. Y. Xu, Z. Li, J. Xia, H. Guo, and Y. Huang Synthesis 1984 781
13. Y. Xu, and Z. Li Synthesis 1986 240
14. Y. Xu, J. Xia, and H. Guo Synthesis 1986 691
15. Y. Xu, and J. Zhang J. Chem. Soc., Chem. Commun. 1986 1606
16. Y. Xu, H. Wej, J. Zhang, and G. Huang Tetrahedron Lett. 30 1989 949
17. P. Tavs, and H. Wetkamp Tetrahedron 26 1970 5529
18. M.A. Kazankova, I.G. Trostyanskaya, S.V. Lutsenko, and I.P. Beletskaya Tetrahedron Lett. 40 1999 569
19. L. Kurtz, G. Lee, D. Morgans Jr., M.J. Waldyke, and T. Ward Tetrahedron Lett. 31 1990 6321
20. P. Zhong, X. Huang, and Z.-X. Xiong Synlett 6 1999 721
21. J.-C. Fiaud J. Chem. Soc., Chem. Commun. 1983 1055
22. R. Malet, M. Moreno-Manas, and R. Pleixats Synth. Commun. 22 1992 2219
23. S.N.L. Bennett, and R.G. Hall J. Chem. Soc. Trans. 1 1995 1145
24. T. Imamoto, T. Oshiki, T. Onozawa, M. Matsuo, T. Hikosaka, and M. Yanagawa Heteroatom Chem. 3 1992 563
25. M. Al-Masum, G. Kumuraswamy, and T. Livinghouse J. Org. Chem. 65 2000 4776
26. R.J. Hinkle, P.J. Stang, and M.H. Kowalski J. Org. Chem. 55 1990 5033
27. F.Y. Kwong, and K.S. Chan Chem. Commun. 2000 1069
28. M. Maffei, and G. Buono Phosphorus, Sulfur, Silicon 79 1993 297
29. I.P. Beletskaya, and M.A. Kazankova Russ. J. Org. Chem. 38 2002 1391
30. D. Gelman, L. Jiang, and S.L. Buchwald Org. Lett. 5 2003 2315
31. T. Hirao, T. Masunaga, Y. Ohshiro, and T. Agawa Tetrahedron Lett. 21 1980 3595
32. T. Hirao, T. Masunaga, and N. Yamada Bull. Chem. Soc. Jpn. 55 1982 909
33. For references on the catalytic transfer hydrogenation with hypophosphorous derivatives, see: (a) G. Brieger, and T.J. Nestrick Chem. Rev. 74 1974 567
34. R.A.W. Johnstone, A.H. Wilby, and A.I. Entwistle Chem. Rev. 85 1985 129
35. S.K. Boyer, J. Bach, J. McKenna, and E. Jagdmann Jr. J. Org. Chem. 50 1985 3408
36. R.A.W. Johnstone, and A.H. Wilby Tetrahedron 37 1981 3667
37. R. Sala, G. Doria, and C. Passarotti Tetrahedron Lett. 25 1984 4565
38. B.T. Khai, and A. Arcelli J. Org. Chem. 54 1989 949
39. A.F. Brigas, and R.A.W. Johnstone Tetrahedron 48 1992 7735
40. C.A. Marques, M. Selva, and P. Tundo J. Chem. Soc., Perkin Trans. 1 1993 529
41. B.T. Khai, and A. Arcelli Chem. Ber. 126 1993 2265
42. H. Lei, M.S. Stoakes, and A.W. Schwabacher Synthesis 1992 1255
43. A.W. Schwabacher, and A.D. Stefanescu Tetrahedron Lett. 37 1996 425
44. A.W. Schwabacher, S. Zhang, and W. Davy J. Am. Chem. Soc. 115 1993 6995
45. H. Lei, M.S. Stoakes, K.P.B. Herath, J. Lee, and A.W. Schwabacher J. Org. Chem. 59 1994 4206
46. D.A. Holt, and J.M. Erb Tetrahedron Lett. 30 1989 5393
47. J.-L. Montchamp, and Y.R. Dumond J. Am. Chem. Soc. 123 2001 510
48. Y.R. Dumond, and J.-L. Montchamp J. Organomet. Chem. 653 2002 252
49. Z. Huang, K. Bravo-Altamirano, and J.-L. Montchamp Comptes Rendus Chimie 7/8-9 2004 763
50. S. Deprèle, and J.-L. Montchamp J. Organomet. Chem. 643-644 2002 154
51. S.J. Fitch J. Am. Chem. Soc. 86 1964 61
52. Y.R. Dumond, R.L. Baker, and J.-L. Montchamp Org. Lett. 2 2000 3341
53. Diazoalkanes: (a) N. Tokutake, J. Hiratake, M. Katoh, T. Irie, H. Kato, and J. Oda Bioorg. Med. Chem. 6 1998 1935
54. J. Lloyd, J.B. Schmidt, J.T. Hunt, J.C. Barrish, D.K. Little, and A.A. Tymiak Bioorg. Med. Chem. Lett. 6 1996 1323
55. M.T. Martin, T.S. Angeles, R. Sugasawara, N.I. Aman, A.D. Napper, M.J. Darsley, R.I. Sanchez, P. Booth, and R.C. Titmas J. Am. Chem. Soc. 116 1994 6508
56. A.C. Baillie, C.L. Cornell, B.J. Wright, and K. Wright Tetrahedron Lett. 33 1992 5133
57. Carbodiimides+ROH: (e) D.S. Karanewsky, and M.C. Badia Tetrahedron Lett. 27 1986 1751
58. N.A. Sampson, and P.A. Bartlett J. Org. Chem. 53 1988 4500
59. D.S. Karanewsky, M.C. Badia, D.W. Cushman, J.M. DeForrest, T. Dejneka, M.J. Loots, M.G. Perri, E.W. Petrillo Jr., and J.R. Powell J. Med. Chem. 31 1988 204
60. E.K. Baylis Tetrahedron Lett. 36 1995 9385
61. S. Chen, and J.K. Coward J. Org. Chem. 63 1998 502
62. L. Qiao, F. Nan, M. Kunkel, A. Gallegos, G. Powis, and A.P. Kozikowski J. Med. Chem. 41 1998 3303
63. H.A.M. Willems, G.H. Veeneman, and P. Westerduin Tetrahedron Lett. 33 1992 2075
64. 3: (l) M.C. Allen, W. Fuhrer, B. Tuck, R. Wade, and J.M. Wood J. Med. Chem. 32 1989 1652
65. L.T. Elepina, V.N. Balakhontseva, and E.E. Nifant'ev J. Gen. Chem. USSR 43 1973 1795
66. 2: (n) H.H. Hatt J. Chem. Soc. 1933 776
67. 5: (o) I.A. Natchev Liebigs Ann. Chem. 1988 861
68. 2NEt: (p) S. Chen, C.-H. Lin, C.T. Walsh, and J.K. Coward Bioorg. Med. Chem. Lett. 7 1997 505
69. (q) See also Ref. 13.
70. W. Froestl, S.J. Mickel, G. von Sprecher, P.J. Diel, R.G. Hall, L. Maier, D. Strub, V. Melillo, P.A. Baumann, R. Bernasconi, C. Gentsch, K. Hauser, J. Jaekel, G. Karlsson, K. Klebs, L. Maitre, C. Marescaux, M.F. Pozza, M. Schmutz, M.W. Steinmann, H. van Riezen, A. Vassout, C. Mondadori, H.-R. Olpe, P.C. Waldmeier, and H. Bittiger J. Med. Chem. 38 1995 3313
71. S. Deprèle, and J.-L. Montchamp J. Am. Chem. Soc. 124 2002 9386
72. J.L. Montchamp J. Organomet. Chem. 690 2005 2388
73. E.A. Boyd, A.C. Regan, and K. James Tetrahedron Lett. 35 1994 4223
74. E.A. Boyd, M. Corless, K. James, and A.C. Regan Tetrahedron Lett. 31 1990 2933
75. M. Bujard, V. Gouverneur, and C. Mioskowski J. Org. Chem. 64 1999 2119
76. Abrunhosa-Thomas, I.; Montchamp, J.-L., unpublished results.
77. J. Tsuji Palladium Reagents and Catalysts: Innovations in Organic Synthesis 2002 Wiley New York pp 366-379
78. K. Inomata, and H. Kinoshita E. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 2002 Wiley New York Chapter V.2.3.1
79. K. Tatsumi, R. Hoffmann, A. Yamamoto, and J.K. Stille Bull. Chem. Soc. Jpn. 54 1981 1857
80. T. Hayashi Acc. Chem. Res. 33 2000 354
81. T. Hayashi, H. Iwamura, M. Naito, Y. Matsumoto, Y. Uozumi, M. Miki, and K. Yanagi J. Am. Chem. Soc. 116 1994 775
82. M.J. Gallagher, M.G. Ranasinghe, and I.D. Jenkins Phosphorus, Sulfur, Silicon 115 1996 255
83. M.I. Kabatschnik, E.N. Tsvetkov, and C.-Y. Chang Dokl. Chem. 124-129 1959 309
84. Y.A. Levin, and V.S. Galeev J. Gen. Chem. USSR 37 1967 2604