Palladium-catalyzed reactions of allenes

Chemical Reviews

Volumn 100, Issue 8, 2000, Pages 3067-3125

  Zimmer, Reinhold ^a,c   Dinesh, Chimmanamada U ^a   Nandanan, Erathodiyil ^a   Khan, Faiz Ahmed ^b  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; CARBON; CARBONYLATION; CARBOXYLATION; CATALYSIS; CHEMICAL BONDS; NITROGEN; OXYGEN; PALLADIUM; SELENIUM; SULFUR; SYNTHESIS (CHEMICAL);

ALLENES; CARBON NUCLEOPHILES; HETEROATOM NUCLEOPHILES; PALLADIUM CATALYSIS;

HYDROCARBONS;

EID: 0034245863     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9902796     Document Type: Article

References (258)

1. For reviews, see: (a) The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Wiley: New York, 1980.
2. (b) The Chemistry of Allenes; Landor, S. R., Ed.; Academic Press: London, 1982.
3. (c) Schuster, H. F.; Coppola, G. M. Allenes in Organic Syntheses; Wiley: New York, 1984.
4. (d) Saalfrank, R. W.; Lurz, C.-J. In Houben-Weyl, Methoden der Organischen Chemie, 4th ed.; Thieme Verlag: Stuttgart, 1993; Vol. E 15/3, p 2959.
5. (e) Bruneau, C.; Dixneuf, P. H. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, Chapter 20.
6. Burton, B. S.; von Pechmann, H. Ber. Dtsch. Chem. Ges. 1887, 20, 145-149.
7. Jones, E. R. H.; Mansfield, G. H.; Whiting, M. C. J. Chem. Soc. 1954, 3208-3212.
8. van't Hoff, J. H. La Chimie dans l'Espace; Bazendijk: Rotterdam, 1875; p 29.
9. Staudinger, H.; Ruzicka, L. Helv. Chim. Acta 1924, 7, 177-201.
10. Pasto, D. J. Tetrahedron 1984, 40, 2805-2827.
11. Zimmer, R. Synthesis 1993, 165-178.
12. Zimmer, R.; Khan, F. A. J. Prakt. Chem. 1996, 338, 92-94.
13. Grigg, R.; Sridharan, V. Pure Appl. Chem. 1998, 70, 1047-1057.
14. Lautens, M.; Rovis, T.; Smith, N. D.; Ostrovsky, D. Pure Appl. Chem. 1998, 70, 1059-1064.
15. (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146-151.
16. (b) Heck, R. F. Org. React. 1982, 27, 345-390
17. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985.
18. (d) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4.
19. (e) Tsuji, J. Palladium Reagents and Catalysis: Innovation in Organic Synthesis; Wiley: New York, 1995.
20. (f) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346.
21. (g) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
22. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
23. de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473-2506; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
24. Hiroi, K.; Kato, F. Tohoku Yakka Daigaku Kenkyu Nempo 1996, 43, 1-33.
25. Yamamoto, Y.; Radhakrishnan, U. Chem. Soc. Rev. 1999, 28, 199-207.
26. Schultz, R. G. Tetrahedron 1964, 20, 2809-2813.
27. Lupin, M. S.; Powell, J.; Shaw, B. L. J. Chem. Soc. A 1966, 1687-1691.
28. (a) van Helden, R.; Kohll, C. F.; Medema, D.; Verberg, G.; Jonkhoff, T. Recl. Trav. Chim. Pays-Bas 1968, 87, 961-991.
29. (b) Medema, D.; van Helden, R.; Kohll, C. F. Inorg. Chim. Acta 1969, 3, 255-265.
30. (c) Stevens, R. R.; Shier, G. D. J. Organomet. Chem. 1970, 21, 495-499.
31. (d) Medema, D.; van Helden, R. Recl. Trav. Chim. Pays-Bas 1971, 90, 304-323.
32. (e) Hughes, R. P.; Powell, J. J. Organomet. Chem. 1972, 34, C51-C54.
33. (f) Hughes, R. P.; Powell, J. J. Organomet. Chem. 1973, 60, 409-425.
34. (g) Ban, E.; Hughes, R. P.; Powell, J. J. Organomet. Chem. 1974, 69, 455-472.
35. Rülke, R. E.; Kliphuis, D.; Elsevier, C. J.; Fraanje, J.; Goubitz, K.; van Leeuwen, P. W. N. M.; Vrieze, K. J. Chem. Soc., Chem. Commun. 1994, 1817-1819.
36. Delis, J. G. P.; Groen, J. H.; Vrieze, K.; van Leeuwen, P. W. N. M.; Veldman, N.; Spek, A. L. Organometallics 1997, 16, 551-562.
37. Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233-236.
38. Hegedus, L. S.; Kambe, N.; Tamura, R.; Woodgate, P. D. Organometallics 1983, 2, 1658-1661.
39. Hegedus, L. S.; Kambe, N.; Ishii, Y.; Mori, A. J. Org. Chem. 1985, 50, 2240-2243.
40. Coulson, D. R. J. Org. Chem. 1973, 38, 1483-1490.
41. Chatani, N.; Takeyasu, T.; Hanafusa, T. Tetrahedron Lett. 1986, 27, 1841-1844.
42. Yamamoto, Y.; Al-Masum, M.; Fujiwara, N.; Asao, N. Tetrahedron Lett. 1995, 36, 2811-2814.
43. Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019-6020.
44. Yamamoto, Y. Pure Appl. Chem. 1996, 68, 9-14.
45. Besson, L.; Goré, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3853-3856.
46. Yamamoto, Y.; Al-Masum, M. Synlett 1995, 969-970.
47. Yamamoto, Y.; Al-Masum, M.; Takeda, A. Chem. Commun. 1996, 831-832.
48. Yamamoto, Y.; Al-Masum, M.; Fujiwara, N. Chem. Commun. 1996, 381-382.
49. Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156-5157.
50. Trost, B. M.; Kottirsch, G. J. Am. Chem. Soc. 1990, 112, 2816-2818.
51. Hiroi, K.; Kato, F.; Yamagata, A. Chem. Lett. 1998, 397-398.
52. Cazes, B. Pure Appl. Chem. 1990, 62, 1867-1878.
53. (a) Djahanbini, D.; Cazes, B.; Goré, J. Tetrahedron Lett. 1984, 25, 203-206.
54. (b) Djahanbini, D.; Cazes, B.; Goré, J. Tetrahedron 1987, 43, 3441-3452.
55. Cazes, B.; Djahanbini, D.; Goré, J.; Genêt, J.-P.; Gaudin, J.-M. Synthesis 1988, 983-985.
56. Trost, B. M.; Tour, J. M. J. Org. Chem. 1989, 54, 484-486.
57. Moriya, T.; Furuuchi, T.; Miyaura, N.; Suzuki, A. Tetrahedron 1994, 50, 7961-7968.
58. Kleijn, H.; Westmijze, H.; Meijer, J.; Vermeer, P. Recl. Trav. Chim. Pays-Bas 1983, 102, 378-380.
59. Ahmar, M.; Cazes, B.; Goré, J. Tetrahedron Lett. 1984, 25, 4505-4508.
60. Kopola, N.; Friess, B.; Cazes, B.; Goré, J. Tetrahedron Lett. 1989, 30, 3963-3966.
61. Cazes, B.; Colovray, V.; Goré, J. Tetrahedron Lett. 1988, 29, 627-630.
62. (a) Ahmar, M.; Cazes, B.; Goré, J. Tetrahedron Lett. 1985, 26, 3795-3798.
63. (b) Ahmar, M.; Cazes, B.; Goré, J. Tetrahedron 1987, 43, 3453-3463.
64. Besson, L.; Bazin, J.; Goré, J.; Cazes, B. Tetrahedron Lett. 1994, 35, 2881-2884.
65. Åkermark, B.; Hansson, S.; Krakenberger, B.; Vitagliano, A.; Zetterberg, K. Organometallics 1984, 3, 679-682.
66. Chaptal, N.; Colovray-Gotteland, V.; Grandjean, C.; Cazes, B.; Goré, J. Tetrahedron Lett. 1991, 32, 1795-1798.
67. (a) Friess, B.; Cazes, B. Goré, J. Bull. Soc. Chim. Fr. 1992, 129, 273-279.
68. (b) Gamez, P.; Ariente, C.; Goré, J.; Cazes, B. Tetrahedron 1998, 54, 14835-14844.
69. Friess, B.; Cazes, B.; Goré, J. Tetrahedron Lett. 1988, 29, 4089-4092.
70. Vicart, N.; Cazes, B.; Goré, J. Tetrahedron Lett. 1995, 36, 5015-5018.
71. Anies, C.; Cazes, B.; Goré, J. J. Chem. Res. (S) 1996, 116-117.
72. Ni, Z.; Padwa, A. Synlett 1992, 869-870.
73. (a) Gauthier, V.; Cazes, B.; Goré, J. Tetrahedron Lett. 1991, 32, 915-918.
74. (b) Gauthier, V.; Grandjean, C.; Cazes, B.; Goré, J. Bull. Soc. Chim. Fr. 1994, 131, 381-390.
75. Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 1747-1750.
76. Meguro, M.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 7453-7456.
77. Larock, R. C.; Berrios-Peña, N. G.; Fried, C. A. J. Org. Chem. 1981, 56, 2615-2617.
78. Larock, R. C.; He, Y.; Leong, W. W.; Han, X.; Refvik, M. D.; Zenner, J. M. J. Org. Chem. 1998, 63, 2154-2160.
79. (a) Zenner, J. M.; Larock, R. C. J. Org. Chem. 1999, 64, 7312-7322.
80. (b) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482-483.
81. Kato, F.; Hiratsuka, Y.; Mitsui, T.; Watanabe, T.; Hiroi, K. Heterocycles 1999, 50, 83-87.
82. Review: Grigg, R. J. Heterocycl. Chem. 1994, 31, 631-639.
83. Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479-11502.
84. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803-11826.
85. Grigg, R.; Xu, L.-H. Tetrahedron Lett. 1996, 37, 4251-4254.
86. Grigg, R.; Brown, S.; Sridharan, V.; Uttley, M. D. Tetrahedron Lett. 1998, 39, 3247-3250.
87. (a) Tour, J. M.; Negishi, E.-i. J. Am. Chem. Soc. 1985, 107, 8289-8292.
88. (b) Negishi, E.-i.; Zhang, Y.; O'Connor, B. Tetrahedron Lett. 1988, 29, 2915-2918.
89. (c) O'Connor, B.; Zhang, Y.; Negishi, E.-i.; Luo, F. T.; Cheng, J. W. Tetrahedron Lett. 1988, 29, 3903-3906.
90. (d) Zhang, Y.; O'Connor, B.; Negishi, E.-i. J. Org. Chem. 1988, 53, 5588-5590.
91. (e) Zhang, Y.; Negishi, E.-i. J. Am. Chem. Soc. 1989, 111, 3454-3456.
92. (f) Negishi, E.-i.; Iyer, S.; Rousset, C. J. Tetrahedron Lett. 1989, 30, 291-294.
93. (g) Zhang, Y.; Wu, G.; Agnel, G.; Negishi, E.-i. J. Am. Chem. Soc. 1990, 112, 8590-8592.
94. (h) Negishi, E.-i Pure Appl. Chem. 1992, 64, 323-334.
95. Ma, E.; Negishi, E.-i. J. Org. Chem. 1994, 59, 4730-4732.
96. Ma, S.; Negishi, E.-i. J. Am. Chem. Soc. 1995, 117, 6345-6357.
97. Trost, B. M.; Michellys, P.-Y.; Gerusz, V. J. Angew. Chem. 1997, 109, 1837-1839; Angew. Chem., Int. Ed. Engl. 1997, 36, 1750-1753.
98. Trost, B. M.; Michellys, P.-Y.; Gerusz, V. J. Angew. Chem. 1997, 109, 1837-1839; Angew. Chem., Int. Ed. Engl. 1997, 36, 1750-1753.
99. Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 6450-6451.
100. (a) Jeong, I.-Y.; Shiro, M.; Nagao, Y. Heterocycles 2000, 52, 85-89.
101. (b) Jeong, I.-Y.; Nagao, Y. Synlett 1999, 576-578.
102. (c) Jeong, I.-Y.; Nagao, Y. Tetrahedron Lett. 1998, 39, 8677-8680.
103. (d) Jeong, I.-Y.; Lee, W. S.; Goto, S.; Sano, S.; Shiro, M.; Nagao, Y. Tetrahedron 1998, 54, 14437-14454.
104. Besson, L.; Goré, J.; Cazes, B. Tetrahedron Lett. 1995, 36, 3857-3860.
105. Al-Masum, M.; Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 6071-6074.
106. Grigg, R.; Sridharan, V.; Terrier, C. Tetrahedron Lett. 1996, 37, 4221-4224.
107. Grigg, R.; Savic, V. Tetrahedron Lett. 1996, 37, 6565-6568.
108. Grigg, R.; Sridharan, V.; Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903-1904.
109. Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435-438.
110. (a) Jung, M. E. Tetrahedron 1976, 32, 3-31.
111. (b) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119.
112. (a) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393.
113. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
114. Larock, R. C.; Tu, C.; Pace, P. J. Org. Chem. 1998, 63, 6859-6866.
115. Desarbre, E.; Mérour, J.-Y. Tetrahedron Lett. 1996, 37, 43-46.
116. Diederen, J. J. H.; Sinkeldam, R. W.; Frühauf, H.-W.; Hiemstra, H.; Vrieze, K. Tetrahedron Lett. 1999, 40, 4255-4258.
117. Selvakumar, K.; Vancheesan, S. Proc. Indian Acad. Chem. Sci. 1995, 107, 179-187.
118. Diederen, J. J. H.; Frühauf, H.-W.; Hiemstra, H.; Vrieze, K.; Pfeffer, M. Tetrahedron Lett. 1998, 39, 4111-4114.
119. Chengebroyen, J.; Pfeffer, M.; Sirlin, C. Tetrahedron Lett. 1996, 37, 7263-7266.
120. Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 5421-5424.
121. Davies, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85-87.
122. Karstens, W. F. J.; Rutjes, F. P. J. T.; Hiemstra, H. Tetrahedron Lett. 1997, 38, 6275-6278.
123. Karstens, W. F. J.; Stol, M.; Rutjes, F. P. J. T.; Hiemstra, H. Synlett 1998, 1126-1128.
124. Prasad, J. S.; Liebeskind, L. S. Tetrahedron Lett. 1988, 29, 4257-4260.
125. Reissig, H.-U.; Hormuth, S.; Schade, W.; Okala Amombo, M.; Watanabe, T.; Pulz, R.; Hausherr, A.; Zimmer, R. J. Heterocycl. Chem. 2000, in press.
126. Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Osawa, E.; Yamaoka, Y.; Fujii, N.; Ibuka, T. J. Org. Chem. 1999, 64, 2992-2993.
127. Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717-720.
128. Anzai, M.; Toda, A.; Ohno, H.; Takemoto, Y.; Fujii, N.; Ibuka, T. Tetrahedron Lett. 1999, 40, 7393-7397.
129. Kang, S.-K.; Baik, T.-G.; Kulak, A. N. Synlett 1999, 324-326.
130. Kang, S.-K.; Baik, T.-G.; Hur, Y. Tetrahedron 1999, 55, 6863-6870.
131. Kimura, M.; Fugami, K.; Tanaka, S.; Tamara, Y. J. Org. Chem. 1992, 57, 6377-6379.
132. Kimura, M.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 3764-3772.
133. (a) Kimura, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. Tetrahedron Lett. 1991, 32, 6359-6362.
134. (b) Kimura, M.; Tanaka, S.; Tamaru, Y. Bull. Chem. Soc. Jpn. 1995, 68, 1689-1705.
135. (a) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: New York, 1982; Vol. 8, pp 799-938.
136. (b) Tsuji, J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley, New York, 1985; Vol. 3, p 163.
137. (c) Trost, B. M. Angew. Chem. 1989, 101, 1199-1219; Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
138. (c) Trost, B. M. Angew. Chem. 1989, 101, 1199-1219; Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
139. Shier, G. D. J. Organomet. Chem. 1967, 10, P15-P17.
140. Inoue, Y.; Ohtsuka, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 3345-3346.
141. Rutjes, F. P. J. T.; Kooistra, T. M.; Hiemstra, H.; Schoemaker, H. E. Synlett 1998, 192-194.
142. Ovaa, H.; Leeuwenburgh, M. A.; Overkleeft, H. S.; van der Marcel, G. A.; van Boom, J. H. Tetrahedron Lett. 1998, 39, 3025-3028.
143. Al-Masum, M.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 3809-3810.
144. Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274-5284.
145. Walkup, R. D.; Guan, L.; Mosher, M. D.; Kim, S. W.; Kim, Y. S. Synlett 1993, 88-90.
146. Kang, S.-K.; Yamaguchi, T.; Pyun, S.-J.; Lee, Y.-T.; Baik, T.-G. Tetrahedron Lett. 1998, 39, 2127-2130.
147. Ma, S.; Zhao, S. J. Am. Chem. Soc. 1999, 121, 7943-7944.
148. Jonasson, C.; Bäckvall, J.-E. Tetrahedron Lett. 1998, 39, 3601-3604.
149. Ma, S.; Sha, Z. J. Org. Chem. 1998, 63, 6387-6389.
150. Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599-7602.
151. Vicart, N.; Cazes, B.; Goré, J. Tetrahedron 1996, 52, 9101-9110.
152. Kamijo, S.; Al-Masum, M.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 691-694.
153. Dzhemilev, U. M.; Kunakova, R. V. J. Organomet. Chem. 1993, 455, 1-27.
154. Ogawa, A.; Kawakami, J.-i.; Sonoda, N.; Hirao, T. J. Org. Chem. 1996, 61, 4161-4163.
155. Ogawa, A.; Kudo, A.; Hirao, T. Tetrahedron Lett. 1998, 39, 5213-5216.
156. (a) Thompson, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 1015-1043.
157. (b) Ojima, I. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1989; Vol. 1, pp 51-97.
158. Groen, J. H.; Elsevier, C. J.; Vrieze, K.; Smeets, W. J. J.; Spek, A. L. Organometallics 1996, 15, 3445-3455.
159. (a) Susuki, T.; Tsuji, J. Bull. Chem. Soc. Jpn. 1968, 41, 1954-1958.
160. (b) Jacobs, T. L. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: New York, 1982; Vol. 2, pp 277-347.
161. Alper, H.; Hartstock, F. H.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905-906.
162. Piotti, M. E.; Alper, H. J. Org. Chem. 1994, 59, 1956-1957.
163. Nokami, J.; Maihara, A.; Tsuji, J. Tetrahedron Lett. 1990, 31, 5629-5630.
164. Darcel, C.; Bruneau, C.; Dixneuf, P. H. Synlett 1996, 218-220.
165. Grigg, R.; Monteith, M.; Sridharan, V.; Terrier, C. Tetrahedron 1998, 54, 3885-3894.
166. Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609-2612.
167. Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479-11502.
168. Grigg, R.; Brown, S.; Sridharan, V.; Uttley, M. D. Tetrahedron Lett. 1997, 38, 5031-5034.
169. Grigg, R.; Pratt, R. Tetrahedron Lett. 1997, 38, 4489-4492.
170. (a) Okuro, K.; Alper, H. J. Org. Chem. 1997, 62, 1566-1567.
171. (b) Xiao, W.-J.; Alper, H. J. Org. Chem. 1999, 64, 9646-9652.
172. Gallagher, T.; Davies, I. W.; Jones, S. W.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Shaw, R. W.; Vernon, P. J. Chem. Soc., Perkin Trans, 1 1992, 433-440.
173. Lathbury, D.; Vernon, P.; Gallagher, T. Tetrahedron Lett. 1986, 27, 6009-6012.
174. Fox, D. N. A.; Gallagher, T. Tetrahedron 1990, 46, 4697-4710.
175. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Gallagher, T. J. Am. Chem. Soc. 1991, 113, 2652-2656.
176. Walkup, R. D.; Park, G. Tetrahedron Lett. 1987, 28, 1023-1026.
177. Walkup, R. D.; Park, G. J. Am. Chem. Soc. 1990, 112, 1597-1603.
178. Walkup, R. D.; Mosher, M. D. Tetrahedron 1993, 49, 9285-9294.
179. Walkup, R. D.; Mosher, M. D. Tetrahedron Lett. 1994, 35, 8545-8548.
180. Walkup, R. D.; Guan, L.; Kim, Y. S.; Kim, S. W. Tetrahedron Lett. 1995, 36, 3805-3808.
181. Kimura, M.; Saeki, N.; Uchida, S.; Harayama, H.; Tanaka, S.; Fugami, K.; Tamaru, Y. Tetrahedron Lett. 1993, 34, 7611-7614.
182. Trost, B. M. Science 1991, 254, 1471.
183. Doi, T.; Yanagisawa, A.; Nakanishi, S.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1996, 61, 2602-2603.
184. Doi, T.; Takasaki, M.; Nakanishi, S.; Yanagisawa, A.; Yamamoto, K.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 2929-2935.
185. Murakami, M.; Itami, K.; Ito, Y. Angew. Chem. 1998, 110, 3616-3619; Angew. Chem., Int. Ed. Engl. 1998, 37, 3418-3420.
186. Murakami, M.; Itami, K.; Ito, Y. Angew. Chem. 1998, 110, 3616-3619; Angew. Chem., Int. Ed. Engl. 1998, 37, 3418-3420.
187. Tsuda, T.; Yamamoto, T.; Saegusa, T. J. Organomet. Chem. 1992, 429, C46-C48.
188. Döhring, A.; Jolly, P. W. Tetrahedron Lett. 1980, 21, 3021-3024.
189. Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 563-593.
190. Killing, H.; Mitchell, T. N. Organometallics 1984, 3, 1318-1320.
191. Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969-978.
192. Mitchell, T. N.; Schneider, U. J. Organomet. Chem. 1991, 407, 319-327.
193. For a review, see: Mitchell, T. N. Synthesis 1992, 803-815.
194. Kwetkat, K.; Riches, B. H.; Rosset, J.-M.; Brecknell, D. J.; Byriel, K.; Kennard, C. H. L.; Young, D. J.; Schneider, U.; Mitchell, T. N.; Kitching, W. Chem. Commun. 1996, 773-774.
195. Koerber, K.; Goré, J.; Vatele, J.-M. Tetrahedron Lett. 1991, 32, 1187-1190.
196. Ichinose, Y.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1988, 61, 2693-2695.
197. Lautens, M.; Ostrovsky, D.; Tao, B. Tetrahedron Lett. 1997, 38, 6343-6346.
198. Gevorgyan, V.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2963-2967.
199. Kadota, I.; Kawada, M.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1997, 62, 7439-7446.
200. Mitchell, T. N.; Schneider, U. J. Organomet. Chem. 1991, 405, 195-199.
201. Grigg, R.; Sansano, J. M. Tetrahedron 1998, 52, 13441-13454.
202. Saalfrank, R. W.; Haubner, M.; Deutscher, C.; Bauer, W. Eur. J. Org. Chem. 1999, 2367-2372.
203. Yang, F.-Y.; Wu, M.-Y.; Cheng, C.-H. Tetrahedron Lett. 1999, 40, 6055-6058.
204. Wu, M.-Y.; Yang, F.-Y.; Cheng, C.-H. J. Org. Chem. 1999, 64, 2471-2474.
205. Watanabe, H.; Saito, M.; Sutou, N.; Kishimoto, K.; Inose, J.; Nagai, Y. J. Organomet. Chem. 1982, 225, 343-356.
206. Watanabe, H.; Saito, M.; Sutou, N.; Nagai, Y. J. Chem. Soc., Chem. Commun. 1981, 617-618.
207. Mitchell, T. N.; Schneider, U.; Fröhling, B. J. Organomet. Chem. 1990, 384, C53-C56.
208. Suginome, M.; Ohmori, Y.; Ito, Y. Synlett 1999, 1567-1568.
209. Onozawa, S.-y.; Hatanaka, Y.; Tanaka, M. Chem. Commun. 1999, 1863-1864.
210. Metal-catalyzed Cross-coupling Reaction; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
211. (a) Maier, M. E. Synlett 1995, 13-26.
212. (b) Wang, K. K. Chem. Rev. 1996, 96, 207-222.
213. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518.
214. Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147.
215. Ruitenberg, K.; Heijn, H.; Elsevier: C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451-1452.
216. Ruitenberg, K.; Kleijn, H.; Westmijze, H.; Meijer, J.; Vermeer, P. Recl. Trav. Chim. Pays-Bas 1982, 101, 405-409.
217. Jeffery-Luong, T.; Linstrumelle, G. Tetrahedron Lett. 1980, 27, 5019-5020.
218. Elsevier, C. J.; Mooiweer, H. H.; Kleijn, H.; Vermeer, P. Tetrahedron Lett. 1984, 25, 5571-5572.
219. Elsevier, C. J.; Vermeer, P. J. Org. Chem. 1985, 50, 3042-3045.
220. Saalfrank, R. W.; Haubner, M.; Deutscher, C.; Bauer, W.; Clark, T. J. Org. Chem. 1999, 64, 6166-6168.
221. Wang, Z.; Wang, K. K. J. Org. Chem. 1994, 59, 4738-4742.
222. Jeffery-Luong, T.; Linstrumelle, G. Synthesis 1982, 738-740.
223. Ruitenberg, K.; Kleijn, H.; Meijer, J.; Oostveen, E. A.; Vermeer, P. J. Organomet. Chem. 1982, 224, 399-405.
224. Russell, C. E.; Hegedus, L. S. J. Am. Chem. Soc. 1983, 105, 943-949.
225. Hegedus, L. S.; Sestrick, M. R.; Michaelson, E. T.; Harrington, P. J. J. Org. Chem. 1989, 54, 4141-4146.
226. de Graaf, W.; Boersma, J.; van Koten, G.; Elsevier, C. J. J. Organomet. Chem. 1989, 378, 115-124.
227. Lupin, M. S.; Shaw, B. L. Tetrahedron Lett. 1964, 883-885.
228. Hughes, R. P.; Powell, J. J. Organomet. Chem. 1969, 20, P17-P19.
229. Medema, D.; van Helden, R. Recl. Trav. Chim. Pays-Bas 1971, 90, 324-342.
230. Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615-2616.
231. Hashmi, A. S. K. Angew. Chem. 1995, 107, 1749-1751; Angew. Chem., Int. Ed. Engl. 1995, 34, 1581.
232. Hashmi, A. S. K. Angew. Chem. 1995, 107, 1749-1751; Angew. Chem., Int. Ed. Engl. 1995, 34, 1581.
233. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295-7304.
234. Hashmi, A. S. K.; Schwarz, L. Chem. Ber./Recl. 1997, 130, 1449-1456.
235. (a) Hashmi, A. S. K.; Choi, J.-H.; Bats, J. W. J. Prakt. Chem. 1999, 341, 342-357.
236. (b) Hashmi, A. S. K.; Schwarz, L.; Bats, J. W. J. Prakt. Chem. 2000, 342, 40-51.
237. (a) Marshall, J. A.; Robinson, E. D. J. Org. Chem. 1990, 55, 3450-3451.
238. (b) Marshall, J. A.; Bartley, G. S. J. Org. Chem. 1994, 59, 9, 7169-7171.
239. (c) Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966-5968.
240. Siegel, H.; Hopf, H.; Germer, A.; Binger, P. Chem. Ber. 1978, 111, 3112-3118.
241. Binger, P.; Schuchardt, U. Chem. Ber. 1980, 113, 1063-1071.
242. Stephan, C.; Munz, C.; tom Dieck, H. J. Organomet. Chem. 1994, 468, 273-278.
243. Munz, C.; Stephan, C.; tom Dieck, H. J. Organomet. Chem. 1990, 395, C42-C46.
244. Kacker, S.; Sen, A. J. Am. Chem. Soc. 1997, 119, 10028-10033.
245. Miyaki, N.; Tomita, I.; Endo, T. Macromolecules 1996, 29, 6685-6690.
246. Miyaki, N.; Tomita, I.; Endo, T. J. Polym. Sci. A: Polym. Chem. 1997, 35, 2097-2103.
247. Bäckvall, J.-E.; Jonasson, C. Tetrahedron Lett. 1997, 35, 291-294.
248. Shimizu, I.; Sugiura, T.; Tsuji, J. J. Org. Chem. 1985, 50, 537-539.
249. Zefirov, N. S.; Lukin, K. A.; Timofeeva, A. Y. Zh. Org. Khim. 1987, 23, 2545-2548; Engl. Ed. 2246-2248.
250. Zefirov, N. S.; Lukin, K. A.; Timofeeva, A. Y. Zh. Org. Khim. 1987, 23, 2545-2548; Engl. Ed. 2246-2248.
251. Lukin, K. A.; Zefirov, N. S. Zh. Org. Khim. 1987, 23, 2548-2552; Engl. Ed. 2249-2252.
252. Lukin, K. A.; Zefirov, N. S. Zh. Org. Khim. 1987, 23, 2548-2552; Engl. Ed. 2249-2252.
253. Zefirov, N. S.; Kozhushkov, S. I.; Kuznetsova, T. S.; Lukin, K. A.; Kazimirchik, I. V. Zh. Org. Khim. 1988, 24, 673-678; Engl. Ed. 605-610.
254. Zefirov, N. S.; Kozhushkov, S. I.; Kuznetsova, T. S.; Lukin, K. A.; Kazimirchik, I. V. Zh. Org. Khim. 1988, 24, 673-678; Engl. Ed. 605-610.
255. Coulson, D. R. J. Org. Chem. 1972, 37, 1253-1254.
256. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119 7163-7164.
257. Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, 951-953.
258. Meguro, M.; Yamamoto, Y. J. Org. Chem. 1999, 64, 694-695.