Palladacycles as reactive intermediates

Chemische Berichte

Volumn 130, Issue 11, 1997, Pages 1567-1578

  Dyker, Gerald ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

Domino reactions; Metallacycles; Palladium catalysis; Polycyclic ring systems

Indexed keywords

EID: 0000770954     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971301104     Document Type: Article

References (102)

1. J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995.
2. [2a] A. de Meijere, F. E. Meyer, Angew. Client. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
3. [2b] S. E. Gibson, R. J. Middleton, Contemp. Org. Synth. 1996, J, 447-471.
4. M R Griee, V. Sridharan, P. Stevenson, S. Sukirthalincam, Tetrahedron~m9, 45, 3557-3568.
5. - [3b] D. Brown, R. Grigs, V. Sridharan, V. Tambyrajah, Tetrahedron Lett. 1995, 36, 8137-8140.
6. Cyclopalladated complexes, frequently refered to as palladacycles, are not within the scope of this review (for comparison: A. D. Ryabov, Synthesis 1985, 233-253 and re
7. 2). Otherwise palladium acetylacetonate and complexes with bidentate phosphine ligands would become palladacycles.
8. '51 To the best of our knowledge 6-membered and larger palladacycles have not been isolated or detected by spectroscopic means.
9. [6a] D. E Ames, D. Bull, Tetrahedron 1982, 38, 383-387.
10. - [6b] D. E. Ames, A. Opalko, Synthesis 1983, 234-235. - f&l D. E Ames, A. Opalko, Tetrahedron 1984, 40, 1919-1925.
11. For a related synthesis of a natural product with a central furan ring, see: R. Laschober, T. Kappe, Synthesis 1990, 387-388.
12. [8a] M Pfeffer, J.-R Sutler, M. A. Rotteveel, A. De Cian, J. Fischer, Tetrahedron 1992, 48, 2427-2440.
13. - [8b] M. Pfeffer, Reel. Trav. Cliim. Pays-Bas 1990, 709, 567-576.
14. [8c] F. Maassarani, M. Pfeffer, G. Le Borgne, Organomelallics 1987, 6, 2043-2053.
15. pa] w. Tao, L. J. Silverberg, A. L. Rheingold, R. F. Heck, Organometallics 1989, 8, 2550-2559.
16. - [9b] G. Wu, A. L. Rheingold, S. J. Geib, R. F. Heck, Organometallics 1987, 6, 1941-1946.
17. 2-Bound arene-palladium complexes stabilized by a rigid norbornene framework have been isolated: C.-S. Li, D.-C. Jou, GH. Cheng, Organometallics 1993, 12, 3945-3954.
18. Very few intermolecular cases of the aryl-aryl coupling reaction under dehydrohalogenation are known so far: 2-hydroxybiphenyl is arylated in the 2'-position by iodobenzene under palladium-catalysis;
19. [11a] T. Satoh, T. Itaya, M. Miura, M. Nomura, Cliem. Lett. 1996, 823-824. - Azulene is arylated by iodobenzene and by l-chloro-4-nitrobenzene in the electron-rich 1-position;
20. [11b] G. Dyker, J. Heiermann, J. Körning, K. Opwis, unpublished results.
21. For related intramolecular aryl-aryl coupling reactions with hetarenes, see: 'I2a' T. Kuroda, F. Suzuki, Tetrahedron Lett. 1991, 32, 6915-6918.
22. [12bl A. P. Kozikowski, D. Ma, Tetrahedron Lett. 1991, 32, 3317-3320.
23. I'3' For Ullmann-type cyclization reactions, presumably involving palladacycles, see: l'3a) R. Gricc, A. Teasdale, V. Sridharan, Tetrahedron Lett. 1991,32, 3859-3862.
24. [3b] G. Dyker, J. Org. Chew. 1993, 58,234-238. [13c] S. Pogodin, P. U. Biedermann, I. Agranat, J. Org. Client. 1997, 62, 2285-2287.
25. [14a] o Bringmann, J. R. Jansen, H.-P. Rink, Angew. Chem. 1986, 98, 917-919; Angew. Chem. Int. Ed. Engl. 1986, 25, 913-915.
26. [14b] G. Bringmann, R. Walter, R. Weirich, Augen: Client. 1990, 102, 1006-1019; Angew. Chem. Int. Ed. Engl. 1990, 29, 977.
27. [14c] G. Bringmann, J. R. Jansen, H. Reuscher, M. Rübenacker, K. Peters, H. G. von Schnerine, Tetrahedron Lett. 1990, 31, 643-646.
28. [15a] T Matsumoto, T. Hosoya, K. Suzuki, J. Am. Chem. Soc. 1992, 114, 3568-3570. - I'&l P. P. Deshpande, O. R. Martin, Tetrahedron Lett. 1990, 3l, 6313-6316.
29. [16a] J. E. Rice. Z.-W. Cai, Tetrahedron Lett. 1992, 33, 1675-1678.
30. [16b] J. E. Rice, Z.-W. Cai, J. Org. Chem. 1993, 55,1415-1424.
31. [17a] G Dyte j Körning, P. G. Jones, P. Bubenitschek, Angew. Chem. 1995, 707, 2743-2745; Angew. Chem. Int. Ed. Engl. 1995, 34, 2502-2504.
32. [7b] G. Dyker, J. Körninc, P. Bubenitschek, P. G. Jones, Tetrahedron 1996, 52, 14777-4786.
33. [17c] G. Dyker, J. Körning, P. Bubenitschek, P. G. Jones, J. Chem. Res. (S) 1997, 132-133; J. Chem. Res. (M) 1997, 880-894.
34. G. Dyker, Tetrahedron Lett. 1991, 32, 7241-7242.
35. J. J. Gonzales, N. Garcia, B. Gomez-Lor, A. E. Echavarren, J. Org. Chem. 1997,62, 1286-1291.
36. [20a] D D Henninss, S. Iwasa, V. H. RawaI, J. Org. Chem. 1997, 62, 2-3. - I20a' D. D. Hennings, S. Iwasa, V. H. Rawal, Tetrahedron Lett. 1997, 38, in press.
37. [21a] p Q Amos, D. A. Whiting, J. Chem. Soc., Chem. Commun. 1987, 510-511. - I2lb' S. A. Ahmad-Junan, P. C. Amos, D. A. Whiting, J. Chem. Soc., Perkin Trans l 1992, 539-545.
38. For another Heck-type cyclization where an intermediary 7-membered palladacycle has been suggested, see:
39. [22a] N. Chida, M. Ohtsuka, S. Ogawa, J. Org. Chem. 1993, 58, 4441-4447. [22] M. C. Mclntosh, S. M. Weinreb, J. Org. Chem. 1993, 58, 4823-4832.
40. R. Grigc, V. Loganathan, V. Santhadumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690.
41. For the Heck reaction with α,β-unsaturated carbonyl compounds epimerization via oxo-rc-allyl palladium complexes is assumed:
42. [4a] K. Kondo, M. Sodeoka, M. Mori, M. Shibasaki, Synthesis 1993, 920-930.
43. [24b] G. K. Friestad, B. P. Branchaud, Tetrahedron Lett. 1995, 36, 7047-7050.
44. J. R. Luly, H. Rapoport, J. Org. Chem. 198-4, 49, 1671-1672.
45. por reiated cyclization reactions at enamines, see:
46. [26a] R. Grigg, V. Sridharan, P. Stevenson, T. Worakun, J. Chem. Soc., Chem. Commun. 1986, 1697-1699. - I26bl R. Grigg, V. Sridharan, P. Stevenson, S. Sukirthalingam, T. Worakun, Tetrahedron 1990, 46, 4003-4018.
47. [27a] M A ciufolini, M. E. Browne, Tetrahedron Lett. 1987, 28, 171-174. - I27bl M. A. Ciufolini, H.-B. Qi, M. E. Browne, J. Org. Chem. 1988,55,4151-4153.
48. E. Negishi, Y. Zhang, I. Shimoyama, G. Wu, J. Am. Chem. Soc. 1989, 111, 8018-8020.
49. l29' For a similar carbonylation reaction, see: R. Grigg, V. Sridharan, Tetrahedron Lett. 1993, 34, 7471-7474.
50. I3J G. Balme, D. Bouyssi, Tetrahedron 1994, 50, 403-414.
51. I3'] A. Kalivretenos, J. K. Stille, L. S. Hegedus, J. Org. Chem. 1991, 56, 2883-2894.
52. For other examples of the intramolecular Stille coupling reaction, see:
53. [32a] A. C. Gyorkos, J. K. Stille, L. S. Hegedus, J. Am. Chem. Soc. 1990,112, 8465-8472.
54. - [32bl J. E. Baldwin, R. M. Adlington, S. H. Ramcharitar, Tetrahedron 1992, 48, 2957-2976. - I32cl E. Piers, R. W. Friesen, B. A. Keay, Tetrahedron 1991, 47, 4555-4570.
55. - [32d] M. Hirama, K. Fujiwara, K. Shieematsu, Y. Fukazawa, J. Am. Chem. Soc. 1989, 777, 4120-4122.
56. For an intramolecular Suzuki coupling reaction, see: N. Miyaura, H. Suginome, A. Suzuki, Tetrahedron Lett. 1984, 25, 761-764.
57. K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420.
58. D. Schinzer, J. Kabbara, Synlett 1992, 766-768.
59. J. A. Porco, F. J. Schoenen, T. J. Stout, J. Clardy, S. L. Schreiber, J. Am. Chem. Soc. 1990,112, 7410-7411.
60. For some carbon-heteroatom bond forming processes presumably proceeding via palladacycles, see:
61. [37a] R. C. Larock, E. K. Yum, N. J. Doty, K. K. C. Sham, J. Org. Chem. 1995, 60, 3270-3271. - [37b] R. C. Larock, E. K. Yum, J. Am. Chem. Soc. 1991, 113, 6689-6690.
62. [37c] P. G. Ciattini, E. Morera, G. Ortar, S. S. Rossi, Tetrahedron 1991, 47, 6449-6456.
63. L. F. Tietze, U. Beifuss, Angcw. Chem. 1993,105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
64. [39a] G Dyker) p Nereis P. Siemsen, P. Bubenitschek, P. G. Jones, Chem. Ber. 1996, 729, 1265-1269. - I39bJ G. Dyker, Peter Siemsen, Stefan Sostmann, Anke Wiegand, Ina Dix, P. G. Jones, Chem. Ber.lRecueil 1997, 130, 261-265.
65. [40a] G Dykei; AngeH._ chem. 1992, 104, 1079-1081; Angcw. Chem. Int. Ed Engl. 1992, 31, 1023-1025.
66. - [40b] G. Dyker, Chem. Ber. 199-4, 727, 739-742.
67. For a review on the mechanisms of intramolecular CH-activation, see: A. D. Ryabov, Client. Rev. 1990, 90, 403-424.
68. [42a] A j Canty; Acc cllem Res 1992 25, 83-90.
69. - [42b] A. J. Canty, Platinum Metals Rev. 1993, 37, 2-7.
70. The isolated oxapalladacycle 74 stabilized with triphenyl-phosphine ligands does not react with or//;o-iodoanisol:
71. [43a] D. J. Cardenas, C. Mateo, A. M. Echavarren, Angew. Chem. 1994, 106, 2529-2531; Angew. Chem. Int. Ed. Engl. 1994, 33, 2445. - [43b] C. Mateo, D. J. Cardenas, C. Fernandez-Rivas, A. M. Echavarren, Chem. Eur. J. 1996,2, 1596-1606.
72. t44' An example for the stoichiometric reaction of iodobenzene with a 5-rnembered palladacycle generated in situ has recently been described: M. Catellani, F. Fricnani, A. Ranconi, Angew. Chem. 1997, 709, 142-145; Angew."Chem. Int. Ed. Engl. 1997, 36, 119-122.
73. p Qzawa, T. Hidaka, T. Yamamoto, A. Yamamoto, J. Organomet. Chem. 1987,330, 253-263. - I45bl F. Ozawa, M. Fujimori, T. Yamamoto, A. Yamamoto, Organometallics 1986, 5, 2144-2149.
74. [46a] T Jeffery, Tetrahedron Lett. 1985, 26, 2667-2670. - I46b' M. T. Reetz, G. Lohmer, J. Chem. Soc., Chem. Commun. 1996, 1921-1922. - I46c' H. Bönnemann, W. Brijoux, Catalytically Active Metal Powders and Colloids, in: A. Fürstner (Ed.), Active Metals, VCH, Weinheim 1996, S. 351-379.
75. '47' G. Dyker, unpublished results.
76. '4S'G. Dyker, Angew. Chem. 1994, 706, 117-119; Angew: Chem. Int. Ed. Engl. 1994,55, 103-105.
77. G. Dyker, J. Org. Chem. 1993, 58, 6426-6428.
78. [so] [soa] M Catellani, G. P. Chiusoli, J. Organomet. Chem. 1985, 286, C13-C16.
79. - I50b' O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 707, 1071-1072;
80. Angew. Chem. Int. Ed. Engl 1989, 28, 1037.
81. - I50cl K. Albrecht, O. Reiser. M. Weber, A. de Meijere, Tetrahedron 1994, 50, 383-401. - I50d]
82. M. Catellani, L. Ferioli, Synthesis 1996, 769-772.
83. G. Dyker, J. Körnine, P. G. Jones, P. Bubenitschek, Angev,: Chem. 1993, 705, 1805-1807;
84. Angev. Chem. Int. Ed. Engl. 1993, 32, 1733-1735.
85. - [51b] G. Dyker, J. Körnine, P. G. Jones, P. Bubenitschek, Liebigs. Ann.lRecueil 1997, 203-209.
86. G. Dyker, A. Kellner, Tetrahedron Lett. 1994, 35, 7633-7636.
87. [53a] L. S. Heeedus, W. H. Darlington, C. E. Russell, J. Org. Chem. 1980, 45, 5193-5196.
88. - [5b] C. Carfaena, L. Mariani, A. Musco, G. Sallese, R. Santi, J. Org. Cliem. 1991, 56, 3924-3927.
89. [53c] H. M. R. Hoffmann, A. R. Otte, A. Wilde, Angew. Cltem. 1992,104, 224-225; Angew. Cliem. Int. Ed Engl. 1992,31, 234.
90. [53d) A. R. Otte, A. Wilde, H. M. R. Hoffmann, Angew. Chem. 1994, 706, 1352-1354; Angew. Chem. Int. Ed. Engl. 1994, 33, 1280-1282.
91. [53e] H. M. R. Hoffmann, A. R. Otte, A. Wilde, S. Menzer, D. J. Williams, Angew: Client. 1995, 707, 73-76; Angew. Chem. Int. Ed. Engl. 1995, 34, 100-102.
92. [53f] A. Aranyos, K. J. Szabo, A. M. Castano, J.-E. Bäckvall, Organometallics 1997, 16, 1058-1064.
93. B. M. Trost, Angew. Cliem. 1989, 101, 1199-1219; Angew. Chem. Int. Ed. Engl. 1989,25, 1173.
94. [55a] B M Trostj Acc chem Res 1990 23, 34-42. - '55b' B.
95. M. Trost, M. K. Trost, Tetrahedron Lett. 1991, 30, 3647-3650. - [55c] B. M. Trost, M. K. Trost, J. Am. Cliem. Soc. 1991,113, 1850-1852.
96. [55d] B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
97. A. S. K. Hashmi, F. Naumann, R. Probst, J. W. Bats, Angew Chem. 1997, 709, 127-130; Angew. Cliem. Int. Ed. Engl. 1997, 36, 104-106.
98. B. M. Trost, M. Yanai, K. Hoogsteen, J. Am. Chem. Soc. 1993, 115, 5294-5295. [58] B. M. Trost, G. J. Tanoury, J. Am. Chem. Soc. 1987, 709, 4753-4755.
99. [59) [59aj B M Trost) A s K Hashmi, Angew. Chem. 1993, 705.
100. 1130-1132; Angew. Chem. Int. Ed. Engl. 1993,52, 1085.
101. [159b] B. M. Trost, A. S. K. Hashmi, J. Am. Chem. Soc. 1994, 116, 2183-2184.
102. A. S. K. Hashmi, Angew. Chem. 1995, 707, 1749-1751; Angew. Chem. Int. Ed. Engl. 1995,34, 1581-1583.