Highly selective markovnikov addition of hypervalent H-spirophosphoranes to alkynes mediated by palladium acetate: Generality and mechanism

Bulletin of the Chemical Society of Japan

Volumn 83, Issue 9, 2010, Pages 1086-1099

  Han, Li Biao ^a   Ono, Yutaka ^a   Xu, Qing ^a   Shimada, Shigeru ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION PRODUCTS; DIPHENYLACETYLENE; GENERAL METHOD; H-BONDS; HYDRIDOPALLADIUM; HYDROGEN ATOMS; MECHANISTIC STUDIES; METALLIC PALLADIUM; PALLADIUM ACETATE; PLATINUM COMPLEXES; REACTION MECHANISM; REDUCTIVE ELIMINATION; TERMINAL ALKYNE; THERMAL DECOMPOSITIONS;

ACETYLENE; ADDITION REACTIONS; PALLADIUM; PALLADIUM COMPOUNDS; PHOSPHORUS; PLATINUM; PLATINUM COMPOUNDS; PYROLYSIS; REACTION KINETICS;

ORGANOMETALLICS;

EID: 77956916726     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20100141     Document Type: Article

References (128)

1. C. R. Johnson, T. Imamoto, J. Org. Chem. 1987, 52, 2170.
2. K. M. Pietrusiewicz, M. Zablocka, W. Wisniewski, Phosphorus, Sulfur Silicon Relat. Elem. 1990, 49, 263.
3. L. Horner, H. Lindel, Phosphorus Sulfur Relat. Elem. 1984, 20, 161.
4. K. M. Pietrusiewicz, W. Wisniewski, M. Zablocka, Tetrahedron 1989, 45, 337.
5. D. J. Collins, L. E. Rowley, J. M. Swan, Aust. J. Chem. 1974, 27, 841.
6. Y.M.Polikarpov, B. K. Sacherbalkov, T. Y. Medved, M. I. Kabachnik, Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 2114.
7. K. M. Pietrusiewicz, M. Zablocka, Tetrahedron Lett. 1988, 29, 1991.
8. H. Brunner, S. Limmer, J. Organomet. Chem. 1991, 417, 173.
9. D. Cavalla, S. Warren, Tetrahedron Lett. 1982, 23, 4505.
10. M. I. Kabachnik, T. Y. Medved, Y. M. Polikarpov, K. S. Yudina, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk. 1962, 1584.
11. H. Brunner, S. Limmer, J. Organomet. Chem. 1991, 413, 55.
12. J. Green, in Fire Retardancy of Polymeric Materials, ed. by A. F. Grand, C. A. Wilkie, Marcel Dekker, New York, 2000, pp. 147-170.
13. F. J. Welch, U.S. Patent 3312674, 1967.
14. R. Rabinowitz, Ger. Patent 1241995, 1967;
15. R. Rabinowitz, Chem. Abstr. 1967, 67, 44417d.
16. R. S. Cooper, U.S. Patent 3340477, 1967.
17. C.V.Juelke, L. E. Trapasso, U.S. Patent 3813454, 1974.
18. R. W. Stackman, Ind. Eng. Chem. Prod. Res. Dev. 1982, 21, 328.
19. A. J. Spak, A. J. Yu, U.S. Patent 4088710, 1978
20. J. C. Goswami, U.S. Patent 4560618, 1985.
21. B. Bingöl, W. H. Meyer, M. Wagner, G. Wegner, Macromol. Rapid Commun. 2006, 27, 1719.
22. J. Jin, J. C. H. Hua, U.S. Patent 3925506, 1975.
23. M. Fujimatsu, M. Miura, Japan Patent 86-250155, 1988;
24. M. Fujimatsu, M. Miura, Chem. Abstr. 1989, 110, 9644k.
25. B.S. Fuller, W. D. Ellis, R. M. Rowell, U.S. Patent 5683820, 1997.
26. J. R. Shukla, U.S. Patent 4241125, 1980
27. C.M.Welch, E. J. Gonzales, J. D. Guthrie, J. Org. Chem. 1961, 26, 3270.
28. a)T.Minami, J. Motoyoshiya, Synthesis 1992, 333.
29. M. Mikolajczyk, P. Balczewski, Top. Curr. Chem. 2003, 223, 161.
30. V. M. Dembitsky, A. A.-A. Al Quntar, A. Haj-Yehia, M. Srebnik, Mini-Rev. Org. Chem. 2005, 2, 91.
31. N.N.Girotra, N. L. Wendler, Tetrahedron Lett. 1969, 10, 4647.
32. E. J. Glamkowski, G.Gal, R. Purick, A. J. Davidson, M. Sletzinger, J. Org. Chem. 1970, 35, 3510.
33. X.-Y. Wang, H.-C. Shi, C. Sun, Z.-G. Zhang, Tetrahedron 2004, 60, 10993.
34. E. Ohler, E. Zbiral, M.El-Badawi, Tetrahedron Lett. 1983, 24, 5599.
35. E. Ohler, M. El-Badawi, E.Zbiral, Chem. Ber. 1985, 118, 4099.
36. C. E. Burgos-Lepley, S. A. Mizsak, R. A. Nugent, R. A. Johnson, J. Org. Chem. 1993, 58, 4159.
37. G. D. Duncan, Z.-M. Li, A. B. Khare, C. E. McKenna, J. Org. Chem. 1995, 60, 7080.
38. P. C. B. Page, M. J. McKenzie, J. A. Gallagher, Synth. Commun. 2002, 32, 211.
39. Y. Ono, L.-B. Han, Tetrahedron Lett. 2006, 47, 421
40. M. R. Harnden, A. Parkin, M. J. Parratt, R. M. Perkins, J. Med. Chem. 1993, 36, 1343.
41. Y. G. Smeyers, A. Hernandez- Laguna, F. J. Romero-Sanchez, N. Fernandez-Ibanez, E. Galvez- Ruano, S. Arias-Perez, J. Pharm. Sci. 1987, 76, 753.
42. S. Megati, S. Phadtare, J. Zemlicka, J. Org. Chem. 1992, 57, 2320.
43. H. B. Lazrek, A. Rochdi, H. Khaider, J.-L. Barascut, J.-L. Imbach, J. Balzarini, M.Witvrouw, C. Pannecouque, E. De Clercq, Tetrahedron 1998, 54, 3807.
44. P. W. Smith, A. J. Chamiec, G. Chung, K. N. Cobley, K. Duncan, P. D. Howes, A. R. Whittington, M. R. Wood, J. Antibiot. 1995, 48, 73.
45. S. A. Holstein, D. M. Cermak, D. F. Wiemer, K. Lewis, R. J. Hohl, Bioorg. Med. Chem. 1998, 6, 687.
46. L. H. Chance, J. P. Moreau, U.S. Patent 3910886, 1975.
47. R. K. Haynes, S. C. Vonwiller, T. W. Hambley, J. Org. Chem. 1989, 54, 5162.
48. R. K. Haynes, W. A. Loughlin, T. W. Hambley, J. Org. Chem. 1991, 56, 5785.
49. E. F. Birse, M. D. Ironside, A. W. Murray, Tetrahedron Lett. 1995, 36, 6309.
50. K. Yamashita, T. Oshikawa, H. Imoto, Japan Patent S62-207281, 1987
51. K. Yamashita, T. Oshikawa, H. Imoto, Chem. Abstr. 1988, 108, 167691m.
52. K. Yamashita, H. Imoto, Y. Tamada, T. Oshikawa, Japan Patent H01-45390, 1989
53. K. Yamashita, H. Imoto, Y. Tamada, T. Oshikawa, Chem. Abstr. 1989, 111, 115592x.
54. a)W.Tian, Z. Zhu, Q. Liao, Y. Wu, Bioorg. Med. Chem. Lett. 1998, 8, 1949.
55. A. A.-A. Al-Quntar, O. Baum, R. Reich, M. Srebnik, Arch. Pharm. 2004, 337, 76.
56. X. Wang, L.-B. Han, Japan Patent 2007-070278, 2007
57. X. Wang, L.-B. Han, Chem Abstr. 2007, 146, 330815.
58. X. Wang, L.-B. Han, Japan Patent 2007-137838, 2007
59. X. Wang, L.-B. Han, Chem Abstr. 2007, 146, 23739.
60. X. Wang, L.-B. Han, Japan Patent 2007-063168, 2007
61. X. Wang, L.-B. Han, Chem Abstr. 2007, 146, 317035.
62. B. Aebischer, P. Frey, H.-P. Haerter, P. L. Herrling, W. Mueller, H. J. Olverman, J. C. Watkins, Helv. Chim. Acta 1989, 72, 1043.
63. D. A. Lowe, H. C. Neijt, B. Aebischer, Neurosci. Lett. 1990, 113, 315.
64. H. Potschka, M. Fedrowitz, W. Löscher, Eur. J. Pharmacol. 1999, 374, 175.
65. L.-B. Han, M. Tanaka, J.Am. Chem. Soc. 1996, 118, 1571.
66. As to the background of metal-mediated P(O)-H additions to carbon-carbon unsaturated bonds before our work (Ref. 9), a U.S. patent claimed the addition of (RO)2P(O)H to alkynes by Ni(PR3)2X2 at elevated temperatures. a) K. Lin, U.S. Patent 3681481, 1972.Hirao also briefly claimed inhis paper describing the coupling of (RO)2P(O)H with organichalides that (RO)2P(O)H added to isoprene, though the efficiency was low (10% yield, 150 °C, 20 h).
67. T. Hirao, T. Masunaga, N. Yamada, Y. Ohshiro, T. Agawa, Bull. Chem. Soc. Jpn. 1982, 55, 909.
68. Reviews: a) L.-B. Han, M. Tanaka, Chem. Commun. 1999, 395.
69. L. Coudray, J.-L. Montchamp, Eur. J. Org. Chem. 2008, 3601.
70. D. Prim, J.-M. Campagne, D. Joseph, B. Andrioletti, Tetrahedron 2002, 58, 2041.
71. A. L. Schwan, Chem. Soc. Rev. 2004, 33, 218.
72. D. S. Glueck, Synlett 2007, 2627.
73. V.P. Ananikov, L. L. Khemchyan, I. P. Beletskaya, Synlett 2009, 2375.
74. Selected examples for metal-catalyzed P(O)-H additions: a) S. Kawaguchi, S. Nagata, A. Nomoto, M. Sonoda, A. Ogawa, J. Org. Chem. 2008, 73, 7928.
75. L.-B. Han, N. Choi, M. Tanaka, Organometallics 1996, 15, 3259.
76. L.-B. Han, R. Hua, M. Tanaka, Angew. Chem., Int. Ed. 1998, 37, 94.
77. C.-Q. Zhao, L.-B. Han, M. Tanaka, Organometallics 2000, 19, 4196.
78. L.-B. Han, C.-Q. Zhao, M. Tanaka, J. Org. Chem. 2001, 66, 5929.
79. S. Deprèle, J.-L. Montchamp, J. Am. Chem. Soc. 2002, 124, 9386.
80. A. Allen, Jr., L. Ma, W. Lin, Tetrahedron Lett. 2002, 43, 3707.
81. M. D. Milton, G. Onodera, Y. Nishibayashi, S. Uemura, Org. Lett. 2004, 6, 3993.
82. L.-B. Han, C. Zhang, H. Yazawa, S. Shimada, J. Am. Chem. Soc. 2004, 126, 5080.
83. P. Ribiere, K. Bravo-Altamirano, M. I. Antczak, J. D. Hawkins, J.-L. Montchamp, J. Org. Chem. 2005, 70, 4064.
84. R. A. Stockland, Jr., A. J. Lipman, J. A. Bawiec, III, P. E. Morrison, I. A. Guzei, P. M. Findeis, J. F. Tamblin, J. Organomet. Chem. 2006, 691, 4042.
85. N. Dobashi, K. Fuse, T. Hoshino, J. Kanada, T. Kashiwabara, C. Kobata, S. K. Nune, M. Tanaka, Tetrahedron Lett. 2007, 48, 4669.
86. M. Niu, H. Fu, Y. Jiang, Y. Zhao, Chem. Commun. 2007, 272.
87. L.-B. Han, C.-Q. Zhao, S. Onozawa, M. Goto, M. Tanaka, J. Am. Chem. Soc. 2002, 124, 3842.
88. L.-B. Han, F. Mirzaei, C.-Q. Zhao, M. Tanaka, J. Am. Chem. Soc. 2000, 122, 5407.
89. C.-Q. Zhao, L.-B. Han, M. Goto, M. Tanaka, Angew. Chem., Int. Ed. 2001, 40, 1929.
90. Q. Xu, L.-B. Han, Org. Lett. 2006, 8, 2099.
91. L.-B. Han, Y. Ono, H. Yazawa, Org. Lett. 2005, 7, 2909.
92. L.-B. Han, Y. Ono, S. Shimada, J. Am. Chem. Soc. 2008, 130, 2752.
93. T. Hirai, L.-B. Han, J. Am. Chem. Soc. 2006, 128, 7422.
94. T. Mizuta, C. Miyaji, T. Katayama, J. Ushio, K. Kubo, K. Miyoshi, Organometallics 2009, 28, 539.
95. N. Ajellal, C. M. Thomas, J.-F. Carpentier, Adv. Synth. Catal. 2006, 348, 1093.
96. M. Kalek, J. Stawinski, Organometallics 2007, 26, 5840.
97. M. C. Kohler, T. V.Grimes, X. Wang, T.-R. Cundari, R. A. Stockland, Jr., Organometallics 2009, 28, 1193.
98. M. C. Kohler, R. A. Stockland, Jr., N. P. Rath, Organometallics 2006, 25, 5746.
99. http://katayamakagaku.co.jp/img/p-chemicalproduct2.pdf.
100. L. W. Nesterov, R. A. Sabirova, N. E. Krepisheva, R. I. Mutalapova, Dokl. Akad. Nauk SSSR 1963, 148, 1085. For general reviews see:
101. Pentacoordinated Phopshorus, ed. by R. R. Holmes, ACS, Washington, 1980, Vols. 1 and 2.
102. J. C. Tebby, in Phosphorus-Carbon Hererocyclic Chemistry: The Rise of A New Domain, ed. by F. Mathey, Pergamon, Amsterdam, 2001, Chap. 6.3.
103. T. Kawashima, in Chemistry of Hypervalent Compounds, ed. by K. Akiba, Wiley, New York, 1999, Chap. 6.
104. (RO)2P(O)H exists in two tautomeric forms, P(=O)H and P-OH; the former is dominant in equilibrium: L. A. Hamilton, P. S. Landis, in Organic Phosphorus Compounds, ed. by G. M. Kosolapoff, L.Maier, Wiley, New York, 1972, Vol. 4, Chap. 11.
105. Depending on the substituents, H-spirophosphoranes can also exist as a mixture of 5-coodinated P(V) and 3-coodinate P(III) forms. However, 100% 5-coodinated P(V) form was reported for 3a. D. Bernard, C. Laurenco, R. Burgada, J. Organomet. Chem. 1973, 47, 113.
106. This work was partially presented at the 86th Annual Meeting of the Chemical Society of Japan, Funabashi, March 27-30, 2006
107. L.-B. Han, Y. Ono, Jpn. Kokai Tokkyo Koho 2007-137850 (filled, November 22, 2005
108. opened, June 7, 2007). Only a few alkenyl spirophosphoranes having electron-withdrawing carboxyl groups are known:
109. M. Sanchez, R. Wolf, R. Burgada, F. Mathis, Bull. Soc. Chim. Fr. 1968, 773.
110. C. Laurenço, R. Burgada, Tetrahedron 1976, 32, 2089.
111. R. Burgada, A. Mohri, Phosphorus, Sulfur Silicon Relat. Elem. 1981, 9, 285.
112. For the synthesisof hypervalent phosphoranidometal complexes: a) K. Kajiyama, Y. Hirai, T. Otsuka, H. Yuge, T. K. Miyamoto, Chem. Lett. 2000, 784.
113. K. Kajiyama, T. K. Miyamoto, K. Sawano, Inorg. Chem. 2006, 45, 502.
114. K. Kubo, H. Nakazawa, Y. Ogitani, K.Miyoshi, Bull. Chem. Soc. Jpn. 2001, 74, 1411.
115. H. Nakazawa, K. Kawamura, T. Ogawa, K. Miyoshi, J. Organomet. Chem. 2002, 646, 204.
116. T. Glowiak, W. K. Rybak, A. Skarzynska, Polyhedron 2000, 19, 2667.
117. A. Skarzynska, W. K. Rybak, T. Glowiak, Polyhedron 2001, 20, 2667.
118. K. B. Dillon, Chem. Rev. 1994, 94, 1441.
119. (Trimethylsilyl)acetylene only gave the trans anti- Markovnikov adduct, which was apparently not due to steric but electroniceffect.
120. Acetylene gas for industry use (ca. 96% purity) was used as received without further purification.
121. T. Bailly, R. Burgada, Phosphorus, Sulfur Silicon Relat. Elem. 1994, 86, 217.
122. Similar transformations of 8 to 7 and 10 to 6 have been described in the literature. Similar transformations of 8 to 7:a)D. Bernard, R. Burgada, Tetrahedron Lett. 1973, 14, 3455.
123. A. Munoz, B. Garrigues, M. Koenig, Tetrahedron 1980, 36, 2467. Similar transformations of 10 to 6
124. F. Ramirez, M. Nowakowski, J. F. Marecek, J. Am. Chem. Soc. 1977, 99, 4515.
125. X-ray data of complexes 12 and 14 are available from SI of Ref. 12s.
126. D. E. C. Corbridge, Top. Phosphorus Chem. 1966, 3, 57. For recent reported X-ray data of P(O)-Pd (Pt) complexes see Refs. 12b and 12n.
127. C. A. Jaska, H. Dorn, A. J. Lough, I. Manners, Chem.-Eur. J. 2003, 9, 271.
128. U. Vogel, M. Scheer, Z. Anorg. Allg. Chem. 2001, 627, 1593.