Selective transition metal-promoted carbon-carbon and carbon-heteroatom bond formation. A review

Organic Preparations and Procedures International

Volumn 29, Issue 2, 1997, Pages 137-176

  Rossi, Renzo ^a   Bellina, Fabio ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON;

BOND FORMATION; CARBON CARBONS; CARBON-HETEROATOM BONDS;

TRANSITION METALS;

EID: 0346614633     PISSN: 00304948     EISSN: 19455453     Source Type: Journal    
DOI: 10.1080/00304949709355180     Document Type: Review

References (171)

1. N. A. Bumagin and I. P. Beletskaya, Russ. Chem. Rev., 59, 1174 (1990).
2. Y. Hatanaka and T. Hiyama, Synlett, 845 (1991).
3. A. Erdik, Tetrahedron, 48, 9557 (1992).
4. T. N. Mitchell, Synthesis, 803 (1992).
5. V. N. Kalinin, Synthesis, 413 (1992).
6. C.-J. Li, Chem. Rev., 93, 2033 (1993).
7. L. Hegedus, J. Organomet. Chem., 477, 269 (1994).
8. H. M. Colquhoun, D. J. Thomson and M. V. Twigg, Carbonylation, Plenum Press, New York, (1991).
9. R. Rossi, A. Carpita and F. Beilina, Org. Prep. Proc. Int., 27, 127 (1995).
10. V. Farina, in Comprehensive Organometallic Chemistry II, E. W. Abel, F. G. A. Stone, G. Wilkinson, L. S. Hegedus, Eds., Pergamon, Oxford, Vol 12, 161-240 (1995).
11. J.-F. Fauvarque and A. Jutard, Bull. Chim. Soc. Fr., 765 (1976).
12. D. Milstein and J. K. Stille, J. Am. Chem. Soc., 101, 4981 (1979).
13. A. Gillie and J. K. Stille, J. Am. Chem. Soc., 102, 4933 (1980).
14. G. S. Reddy and W. Tam, Organometallics, 3, 630 (1984).
15. T. Katayama and M. Umeno, Chemistry Lett., 2073 (1991).
16. A. Minato, K. Suzuki, K. Tamao and M. Kumada, Chem. Commun., 511 (1984).
17. A. Minato, K. Tamao, K. Suzuki and M. Kumada, Tetrahedron Lett., 21, 4017 (1980).
18. A. Carpita and R. Rossi, Gazz. Chim. Ital., 115, 575 (1985).
19. R. Rossi, A. Carpita, M. Ciofalo and V. Lippolis, Tetrahedron, 47, 8443 (1991).
20. K. C. Eapen, S. S. Dua and C. Tamborski, J. Org. Chem., 49, 478 (1984).
21. S. W. Wright, D. L. Hageman and L. D. Me Clure, J. Org. Chem., 59, 6095 (1994)
22. D. R. Me Kean, G. Parrinello, A. F. Renaldo and J. K. Stille, J. Org. Chem., 52, 422 (1987).
23. A. Bahl, W. Grahn, S. Stadler, F. Feiner, G. Bourhill, C. Brauchle, A. Reisner and P. G. Jones, Angew. Chem. Int. Ed. Eng., 34, 1485 (1995).
24. E. Dubois and J. M. Beau, Chem. Commun., 1191 (1990)
25. L. Brandsma and H. D. Ver Kruijsse, Synth. Commun., 20, 2275 (1990).
26. J. W. Grissom, T. L. Calkins and M. Egan, J. Am. Chem. Soc., 115, 11744 (1993).
27. Q. Zhou, P. J. Carrol and T. M. Swager, J. Org. Chem,. 59, 1294 (1994).
28. J. W. Grissom, T. L. Calkins, D. Huang and H. McMillen, Tetrahedron, 50, 4635 (1994).
29. S. Cacchi, P. G. Ciattini, E. Morera and G. Ortar, Tetrahedron Lett., 28, 3039 (1987)
30. A.-S. Carlstrom and T. Frejd, J. Org. Chem., 56, 1289 (1991).
31. L. N. Pridgen, J. Org. Chem., 47, 4319 (1982).
32. I. Mangalagiu, T. Benneche, K. Undheim, Tetrahedron Lett., 37, 1309 (1996).
33. L. L. Gundersen, G. Langli and F. Rise, Tetrahedron Lett., 36, 1945 (1995).
34. G. Langli, L.-L. Gundersen and F. Rise, Tetrahedron, 52, 5625 (1996).
35. I. Klement, P. Knöchel, K. Chau and G. Cahiez, Tetrahedron Lett., 35, 1177 (1994).
36. A. Dondoni, M. Fogagnolo, A. Medici and E. Negrini, Synthesis, 185 (1987).
37. I. Kaswasaki, M. Yamashita and S. Ohta, Chem. Commun., 2085 (1994).
38. D. A. Evans and T. Bach, Angew. Chem. Int. Ed. Engl., 32, 1326 (1993).
39. J. W. Tilley and S. Zawoiski, J. Org. Chem., 53, 386 (1988).
40. R. W. Bates, C. J. Gabel and J. Ji, Tetrahedron Lett., 35, 6993 (1994).
41. R. W. Bates and T. Rama-Devi, Synlett, 1151 (1995).
42. S. Torii, L. H. Xu and H. Okumoto, Synlett, 515 (1992).
43. Y. Miura, H. Oka and M. Momoki, Synthesis, 1419 (1995).
44. A. M. Echavarren and J. K. Stille, J. Am. Chem. Soc., 109, 5478 (1987)
45. Y. Yang and A. R. Martin, Synth. Commun., 22, 1757 (1992)
46. B. C. Soderberg, in Comprehensive Organometallic Chemistry II, Pergamon, Oxford, Vol 12, 241-297 (1995).
47. B. M. Trost and T. R. Verhoeven, in Comprehensive Organometallic Chemistry, Pergamon, Oxford, Vol 8, 799-938 (1982).
48. J. Solberg and K. Undheim, Acta Chem. Scand., A43, 62 (1989).
49. A. Sekiya and N. Ishikawa, J. Organomet. Chem., 118, 349 (1976).
50. Y. Ikoma, K. Ando, Y. Naoi, T. Akiyama and A. Sugimori, Synth. Commun., 21, 481 (1991).
51. N. Miyaura, T. Yanagi and A. Suzuki, Commun., 11, 513 (1981).
52. J. C. Anderson and H. Namli, Synlett, 765 (1995).
53. T. Watanabe, N. Miyaura and A. Suzuki, Synlett, 207 (1992).
54. J-m. Fu, M. J. Sharp and V. Snieckus, Tetrahedron Lett., 29, 5459 (1988).
55. M. C. Unrau, M. G. Cambell and V. Snieckus, Tetrahedron Lett., 33, 2773 (1992).
56. R. C. Larock, N. G. Barrios-Peña, C. A. Fried, J. Org. Chem. 56, 2615 (1991).
57. A. Dondoni, G. Fantin, M. Fogagnolo, A. Medici and P. Pedrini, Synthesis, 693 (1987).
58. B. C. Pierce, Synth. Commun., 22, 1627 (1992).
59. J. Solberg and K. Undheim, Acta Chem. Scand., A41, 712 (1987).
60. Y. Kondo, R. Watanabe, T. Sakamoto and Y. Yamanaka, Chem. Pharm. Bull. Jpn., 37, 2814 (1989).
61. V. P. Baillargeon and J. K. Stille, J. Am. Chem. Soc., 108, 452 (1986).
62. Y. Hatanaka, K. Goda, Y. Okahara and T. Hiyama, Tetrahedron, 50, 8301 (1994).
63. M. Ishikura and M. Terashima, J. Org. Chem., 59, 2634 (1994).
64. E. Negishi and D. E. Van Horn, J. Am. Chem. Soc., 99, 3168 (1977).
65. P. L. Heinze and D. J. Burton, J. Org. Chem., 53, 2714 (1988).
66. L. S. Hegedus, M. R. Sestrick, E. T. Michaelson and P. J. Harrington, J. Org. Chem., 54, 4141 (1989).
67. M. Kosugi, T. Sumiya, Y. Obara, M. Suzuki, H. Sano and T. Migita, Bull. Chem. Soc. Jpn., 60, 767 (1987).
68. R. W. Freisen and C. F. Sturino, J. Org. Chem., 55, 2572 (1990).
69. F. Marsais, Ph. Pineau, F. Nivolliers, M. Mallet, A. Turck, A. Godard and G. Queguiner, J. Org. Chem., 57, 565 (1992).
70. H. B. Kwon, B. H. McKee and J. K. Stille, J. Org. Chem., 55, 3114 (1990).
71. G. T. Crisp, and P. T. Glink, Tetrahedron, 50, 3213 (1994).
72. D. M. Hodgson, J. Witherington, B. A. Moloney, I. C. Richards and J.-L. Brayer, Synlett, 32 (1995).
73. G. Shi, Z. Cao and X. Zhang, J. Org. Chem., 60, 6608 (1995).
74. P. N. Lopwe and A. F. Rowe, Comp. Biochem. Physiol., B: Comp Biochem., 88B, 223 (1987).
75. C. Walsh, Tetrahedron, 38, 871 (1982).
76. J. M. Clough, Nat. Prod. Rep., 10, 565 (1993).
77. J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, J. Wiley & Sons, New York, 1990.
78. R. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985.
79. A. Spencer, J. Organomet. Chem., 258, 101 (1983).
80. T. Jeffery, Chem. Commun., 1287 (1984)
81. C. A. Merlic and M. F. Semmelhack, J. Organomet. Chem., 391, C23 (1990).
82. C. Amatore, M. Azzabi and A. Jutand, J. Am. Chem. Soc., 113, 8375 (1991)
83. J. E. Plevyak, J. E. Dickerson and R. F. Heck, J. Org. Chem., 44, 4078 (1979).
84. N. Cortese and R. F. Heck, J. Org. Chem., 42, 3907 (1977).
85. W. Tao, S. Nesbitt, and R. F. Heck, J. Org. Chem., 55, 63 (1990).
86. T. Izumi, Y. Nishimoto, K. Kohei and A. Kasahara, J. Heterocycl. Chem., 27, 1419 (1990).
87. P. C. Amos and D. A. Whiting, Chem. Commun., 510 (1987).
88. A. Satake, K. Okano, I. Shimizu and A. Yamamoto, Synlett, 839 (1994).
89. T. Satoh, T. Itaya, K. Okuro, M. Miura and M. Nomura, J. Org. Chem., 60, 7267 (1995).
90. J. J. Chen, J. A. Walker II, W. Liu, D. S. Wise and L. B. Towsend, Tetrahedron Lett., 36, 8363 (1995).
91. P. J. Harrington, L. S. Hegedus and K. F. McDaniel, J. Am. Chem. Soc., 109, 4335 (1987).
92. T. Jeffery, Tetrahedron Lett., 33, 1989 (1992).
93. K. Albrecht, O. Reiser, M. Weber, B. Knieriem and A. de Meijere, Tetrahedron, 50, 383 (1994).
94. T. Jeffery, Tetrahedron Lett., 26, 2667 (1985).
95. K. Minn, Synlett, 115 (1991).
96. G. J. Quallich, D. E. Fox, R. C. Friedmann and C. W. Murtiashaw, J. Org. Chem., 57, 761 (1992).
97. R. F. Jackson, N. Wishart, A. Wood, K. James and M. J. Wythes, J. Org. Chem., 57, 3397 (1992).
98. J. L. Fraser, R. F. W. Jackson and B. Porter, Synlett, 379 (1994).
99. Y. Tamaru, H. Ochiai, T. Nakamura and Z. Yoshida, Tetrahedron Lett., 27, 955 (1986).
100. E. Nakamura, S. Aoki, K. Sekiya, H. Oshino and I. Kuwajima, J. Am. Chem. Soc., 109, 8056 (1987).
101. I. Klement, P. Knochel, K. Chau and G. Cahiez, Tetrahedron Lett., 35, 1177 (1994).
102. M. Kosugi, M. Suzuki, I. Hagiwara, K. Goto; K. Saitoh and T. Migita, Chemistry Lett., 939 (1982).
103. M. Kosugi, M. Ishiguro, Y. Negishi, H. Sano and T. Migita, Chemistry Lett., 1511 (1984).
104. M. Kosugi, T. Sumiya, K. Ohhashi, H. Sano and T. Migita, Chemistry Lett., 997 (1985).
105. M. Kosugi, Y. Negishi, M. Kameyama and T. Migita, Bull. Chem. Soc. Jpn., 58, 3383 (1985).
106. M. Durandetti, S. Sibille, J?-Y. Nedelec and J. Peridiou, Synth. Commun., 24, 1245 (1994).
107. A. Loffler and G. Himbert, Synthesis, 495 (1992).
108. T. L. Draper and T. R. Bailey, J. Org. Chem., 60, 748 (1995).
109. G. T. Crisp and T. A. Robertson, Tetrahedron, 48, 3239 (1992).
110. A. Arcadi, S. Cacchi, F. Marinelli, P. Pace and G. Sanzi, Synlett, 823 (1995).
111. M. J. Chapdelaine, P. J. Warwick and A. Shaw, J. Org. Chem., 54, 1218 (1989).
112. M. Kosugi, M. Kameyama and T. Migita, Chemistry Lett., 927 (1983).
113. D. Baranano and J. F. Flartwig, J. Am. Chem. Soc., 117, 2937 (1995).
114. A. Minato, K. Suzuki and T. Tamao, J. Am. Chem. Soc., 109, 1257 (1987).
115. R. Rossi and A. Carpita, Tetrahedron Lett., 27, 2529 (1986).
116. A. Carpita and R. Rossi, Tetrahedron Lett., 27, 4351 (1986).
117. B. P. Andreini, A. Carpita and R. Rossi, Tetrahedron Lett., 27, 6633 (1986).
118. B. P. Andreini, M. Benetti, A. Carpita and R. Rossi, Tetrahedron, 43, 4591 (1987).
119. B. P. Andreini, A. Carpita and R. Rossi, Tetrahedron Lett., 29, 2239 (1988).
120. B. P. Andreini, M. Benetti, A. Carpita and R. Rossi, Gazz. Chim. Ital., 118, 469 (1988).
121. A. Carpita, R. Rossi and B. Scamuzzi, Tetrahedron Lett., 30, 2699 (1989).
122. B. P. Andreini, A. Carpita, R. Rossi and B. Scamuzzi, Tetrahedron, 30, 5621 (1989).
123. A. Minato, J. Org. Chem., 56, 4052 (1991).
124. V. Ratovelomanana, A. Hammoud and G. Linstrumelle, Tetrahedron Lett., 28, 1649 (1987).
125. W. R. Roush and R. Riva, J. Org. Chem., 53, 710 (1988).
126. N. Miyaura, K. Yamada, H. Suginome and A. Suzuki, J. Am. Chem. Soc, 107, 972 (1985).
127. J. Uenishi, J.-M. Beau, R. W. Armstrong and Y. Kishi, J. Am. Chem. Soc, 109, 4576 (1987).
128. W. R. Roush, K. J. Moriarty and B. B. Brown, Tetrahedron Lett., 31, 6509 (1990).
129. J. E. Baldwin, R. Chesworth, J. S. Parker and A. T. Russell, Tetrahedron Lett., 36, 9551 (1995).
130. M. Alami, B. Crousse and G. Linstrumelle, Tetrahedron Lett., 36, 3687 (1995).
131. S. Torii, H. Okumoto, T. Tadokoro, A. Nishimura and Md. A. Rashid, Tetrahedron Lett., 34, 2139 (1993).
132. A. Bryant-Friederich and R. Neidlein, Synthesis, 1506 (1995).
133. V. Ratovelomanana and G. Linstrumelle, Tetrahedron Lett., 22, 315 (1981).
134. D. Guillerm and G. Linstrumelle, Tetrahedron Lett., 26, 3811 (1985).
135. D. Guillerm and G. Linstrumelle, Tetrahedron Lett., 27, 5857 (1986).
136. P. Magnus, H. Annoura and J. Harling, J. Org. Chem., 55, 1709 (1990).
137. C. Creusy and J.-M. Beau, Tetrahedron Lett., 32, 3171 (1991).
138. M. Avignon-Tropis, J. M. Beijeaud, J. R. Pougny, I. Frechard-Ortuno, D. Guillerm and G. Linstrumelle, J. Org. Chem., 57, 651 (1992).
139. D. Chemin, M. Alami and G. Linstrumelle, Tetrahedron Lett., 33, 2681 (1992).
140. H. Audrain, T. Skrydstrup, G. Ulibarri, C. Riche, A. Chiaroni and D. S. Grierson, Tetrahedron, 50, 1469 (1994).
141. M.-J. Wu, C.-F. Lin, J.-S. Wu and H.-T. Chen, Tetrahedron Lett., 35, 1879 (1994).
142. T. Nishikawa, A. Ino and M. Isobe, Tetrahedron, 50, 1449 (1994).
143. G. McGaffin and A. de Meijere, Synthesis, 583 (1994).
144. Y. Sakai, E. Nishiwaki, K. Shishido, M. Shibuya and M. Kido, Tetrahedron Lett., 32, 4363 (1991).
145. D. Elbaum, T. B. Nguyen, W. L. Jorgesen and S. L. Schreiber, Tetrahedron, 50, 1503 (1994).
146. T. Nishikawa, A. Ino and M. Isobe, Tetrahedron, 50, 1449 (1994).
147. D. Chemin and G. Linstrumelle, Tetrahedron, 50, 5335 (1994)
148. M. Alami, B. Crousse and G. Linstrumelle, Tetrahedron Lett., 35, 3543 (1994).
149. V. Ratevelomanana and G. Linstrumelle, Tetrahedron Lett., 25, 6001 (1984).
150. A. Carpita, D. Neri and R. Rossi, Gazz. Chim. Ital., 117, 503 (1987).
151. E. Negishi, N. Okukado, S. F. Lovich and F-T. Luo, J. Org. Chem., 49, 2629 (1984).
152. J. P. Gillet, R. Sauvètre and J. F. Normant, Tetrahedron Lett., 26, 3999 (1985)
153. F. Tellier, R. Sauvètre and J. F. Normant, J. Organomet. Chem., 303, 309 (1986).
154. F. Tellier, R. Sauvètre and J. F. Normant, J. Organomet. Chem., 328, 1 (1987).
155. F. Tellier, R. Sauvètre and J. F. Normant, J. Organomet. Chem., 367, 1 (1989).
156. F. Tellier, R. Sauvètre and J. F. Normant, J. Organomet. Chem., 292, 19 (1985).
157. S. Eddarir, H. Mestdagh and C. Rolando, Tetrahedron Lett., 32, 69 (1991).
158. A. G. Myers, M. M. Alauddin, M. A. M. Fuhry, P. S. Dragovich, N. S. Finney and P. M. Harrington, Tetrahedron Lett., 30, 6997 (1989).
159. F. Beilina, A. Carpita, M. De Santis and R. Rossi, Tetrahedron Lett., 35, 6913 (1994).
160. F. Beilina, A. Carpita, M. De Santis and R. Rossi, Tetrahedron, 50, 12029 (1994).
161. R. Rossi, F. Beilina, A. Carpita and R. Gori, Synlett, 344 (1995).
162. R. Rossi, F. Beilina, A. Carpita and R. Gori, Gazz. Chim. Ital., 125, 381 (1995).
163. F. Beilina, A. Carpita and R. Rossi, Convegno Nazionale su Orientamenti e Metodologie in Chimica Farmaceutica, Organica e Bioorganica, Numana (AN), Italy, June 2-6, 1995, Atti del Convegno, 021.
164. R. Rossi, F. Bellina, A. Carpita and F. Mazzarella, Tetrahedron, 52, 4095 (1996).
165. S. Murahashi, M. Yamamura, K. Yanagisawa, N. Mita and K. Kondo, J. Org. Chem., 44, 2408 (1979).
166. H. J. Cristau, B. Chabaud, B. Labaudiniere and H. Christol, J. Org. Chem., 51, 875 (1986).
167. N. A. Bumagin, Yu. V. Gulevich and I. P. Beletskaya, Izv. Akad Nauk SSSR, Ser. Khim., 4, 953 (1984).
168. M. Kosugi, T. Ogata, M. Terada, H. Sano and T. Migita, Bull. Soc. Chem. Jpn., 57, 1863 (1984).
169. R. Rossi, F. Beilina and A. Carpita, Synlett, 356 (1996).
170. R. Rossi and F. Beilina, Invited lecture at the 1st Korea-Italy Symposium in Medicinal Chemistry, Seoul, Korea, May 24-25, 1996.
171. R. Rossi and F. Bellina, Unpublished results.