Sequential insertion of alkynes and CO or isocyanides into the Pd-C bond of cyclopalladated phenylacetamides. Synthesis of eight-membered palladacycles, benzo[d]azocine-2,4(1 H,3 H)-diones, and highly functionalized acrylonitrile and acrylamide derivatives

Organometallics

Volumn 31, Issue 8, 2012, Pages 3361-3372

  Frutos Pedreño, Roberto ^a   González Herrero, Pablo ^a   Vicente, José ^a   Jones, Peter G ^b  

^a UNIVERSITY OF MURCIA   (Spain)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDES; CYANOCOMPLEXES; CYCLOPALLADATED COMPLEXES; FUNCTIONALIZED; IN-SITU; ISOCYANIDES; LOW-YIELD; MOLAR RATIO; PALLADACYCLES; REDUCTIVE COUPLINGS; REFLUXING; SEQUENTIAL INSERTION;

ACETYLENE; AMIDES; BARIUM COMPOUNDS; CARBON DIOXIDE; CHLORINE COMPOUNDS; CYANIDES; ORGANOMETALLICS;

PALLADIUM COMPOUNDS;

EID: 84860324009     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300151n     Document Type: Article

References (88)

1. Dupont, J.; Pfeffer, M. Palladacycles. Synthesis, Characterization and Applications; Wiley-VCH: Weinheim, 2008.
2. Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527-2571
3. Beletskaya, I. P.; Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055-4082
4. Omae, I. Coord. Chem. Rev. 2004, 248, 995-1023
5. Wu, G.; Rheingold, A. L.; Heck, R. F. Organometallics 1987, 6, 2386-2391
6. Maassarani, F.; Pfeffer, M.; Le, B. G. J. Chem. Soc., Chem. Commun. 1987, 565-567
7. Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169-1171
8. Wu, G.; Geib, S. J.; Rheingold, A. L.; Heck, R. F. J. Org. Chem. 1988, 53, 3238-3241
9. Tao, W.; Silverberg, L. J.; Rheingold, A. L.; Heck, R. F. Organometallics 1989, 8, 2550-2559
10. Dupont, J.; Pfeffer, M.; Rotteveel, M. A.; De, C. A.; Fischer, J. Organometallics 1989, 8, 1116-1118
11. Dupont, J.; Pfeffer, M.; Theurel, L.; Rotteveel, M. A.; De, C. A.; Fischer, J. New J. Chem. 1991, 15, 551-558
12. Beydoun, N.; Pfeffer, M.; DeCian, A.; Fischer, J. Organometallics 1991, 10, 3693-3697
13. Pfeffer, M.; Rotteveel, M. A.; Le, B. G.; Fischer, J. J. Org. Chem. 1992, 57, 2147-2154
14. Pfeffer, M. Pure Appl. Chem. 1992, 64, 335-342
15. Pfeffer, M.; Sutter, J. P.; Rotteveel, M. A.; De, C. A.; Fischer, J. Tetrahedron 1992, 48, 2427-2440
16. Pfeffer, M.; Sutter, J. P.; DeCian, A.; Fischer, J. Organometallics 1993, 12, 1167-1173
17. Maassarani, F.; Pfeffer, M.; Spencer, J.; Wehman, E. J. Organomet. Chem. 1994, 466, 265-271
18. Vicente, J.; Abad, J.-A.; Gil-Rubio, J.; Jones, P. G. Organometallics 1995, 14, 2677-2688
19. Vicente, J.; Saura-Llamas, I.; Ramírez de Arellano, M. C. J. Chem. Soc., Dalton Trans. 1995, 2529-2533
20. Vicente, J.; Saura-Llamas, I.; Palin, M. G.; Jones, P. G. J. Chem. Soc., Dalton Trans. 1995, 2535-2547
21. Vicente, J.; Abad, J.-A.; Gil-Rubio, J. Organometallics 1996, 15, 3509-3519
22. Vicente, J.; Abad, J.-A.; Shaw, K. F.; Gil-Rubio, J.; Ramírez de Arellano, M. C.; Jones, P. G. Organometallics 1997, 16, 4557-4566
23. Vicente, J.; Saura-Llamas, I.; Turpín, J.; Ramírez de Arellano, M. C.; Jones, P. G. Organometallics 1999, 18, 2683-2693
24. Maassarani, F.; Pfeffer, M.; Le, B. G. Organometallics 1987, 6, 2029-2043
25. Spencer, J.; Pfeffer, M. Tetrahedron: Asymmetry 1995, 6, 419-426
26. Maassarani, F.; Pfeffer, M.; Le, B. G. Organometallics 1987, 6, 2043-2053
27. Gül, N.; Nelson, J. H.; Willis, A. C.; Rae, A. D. Organometallics 2002, 21, 2041-2048
28. Vicente, J.; Saura-Llamas, I.; Turpín, J.; Bautista, D.; Ramírez de Arellano, M. C.; Jones, P. G. Organometallics 2009, 28, 4175-4195
29. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644-4680
30. Majhi, T. P.; Achari, B.; Chattopadhyay, P. Heterocycles 2007, 71, 1011-1052
31. Shiina, I. Chem. Rev. 2006, 107, 239-273
32. Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95-102
33. Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077
34. Evans, P. A.; Holmes, B. Tetrahedron 1991, 47, 9131-9166
35. Ma, S.; Gu, Z. J. Am. Chem. Soc. 2006, 128, 4942-4943
36. Ohno, H.; Hamaguchi, H.; Ohata, M.; Kosaka, S.; Tanaka, T. J. Am. Chem. Soc. 2004, 126, 8744-8754
37. Trost, B. M.; Ameriks, M. K. Org. Lett. 2004, 6, 1745-1748
38. Cropper, E. L.; White, A. J. P.; Ford, A.; Hii, K. K. J. Org. Chem. 2006, 71, 1732-1735
39. Voskressensky, L. G.; Listratova, A. V.; Borisova, T. N.; Alexandrov, G. G.; Varlamov, A. V. Eur. J. Org. Chem. 2007, 6106-6117
40. Jiang, X. P.; Yang, Q.; Yu, Y. H.; Fu, C. L.; Ma, S. M. Chem.-Eur. J. 2009, 15, 7283-7286
41. Majumdar, K. C.; Chattopadhyay, B. Curr. Org. Chem. 2009, 13, 731-757
42. Majumdar, K. C.; Ghosh, T.; Chakravorty, S. Tetrahedron Lett. 2010, 51, 3372-3375
43. Boeckman, R. K.; Genung, N. E.; Chen, K.; Ryder, T. R. Org. Lett. 2010, 12, 1628-1631
44. Majumdar, K. C. RSC Adv. 2011, 1, 1152-1170
45. Vicente, J.; Saura-Llamas, I.; García-López, J. A.; Bautista, D. Organometallics 2010, 29, 4320-4338
46. Vicente, J.; González-Herrero, P.; Frutos-Pedreño, R.; Chicote, M. T.; Jones, P. G.; Bautista, D. Organometallics 2011, 30, 1079-1093
47. Hernández, R.; Melián, D.; Prangé, T.; Suárez, E. Heterocycles 1995, 41, 439-454
48. Dorta, R. L.; Francisco, C. G.; Suárez, E. Tetrahedron Lett. 1994, 35, 1083-1086
49. Hernández, R.; Marrero, J. J.; Melián, D.; Suárez, E. Tetrahedron Lett. 1988, 29, 6661-6664
50. Yoshifuji, S.; Arakawa, Y.; Nitta, Y. Chem. Pharm. Bull. 1987, 35, 357-363
51. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr 2008, 64, 112-122
52. Spencer, J.; Pfeffer, M.; Kyritsakas, N.; Fischer, J. Organometallics 1995, 14, 2214-2224
53. Yin, J. J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101-1104
54. Giandomenico, C. M.; Hanau, L. H.; Lippard, S. J. Organometallics 1982, 1, 142-148
55. Greco, G. E.; O'Donoghue, M. B.; Seidel, S. W.; Davis, W. M.; Schrock, R. R. Organometallics 2000, 19, 1132-1149
56. Crociani, B.; Nicolini, M.; Richards, R. L. Inorg. Chim. Acta 1975, 12, 53-59
57. Adams, C. J.; Anderson, K. M.; Bartlett, I. M.; Connelly, N. G.; Orpen, A. G.; Paget, T. J. Organometallics 2002, 21, 3454-3463
58. Bell, A.; Lippard, S. J.; Roberts, M.; Walton, R. A. Organometallics 1983, 2, 1562-1572
59. Bell, A.; Walton, R. A. J. Organomet. Chem. 1984, 263, 359-369
60. Cabon, N.; Paugam, E.; Petillon, F. Y.; Schollhammer, P.; Talarmin, J.; Muir, K. W. Organometallics 2003, 22, 4178-4180
61. Dewan, J. C.; Giandomenico, C. M.; Lippard, S. J. Inorg. Chem. 1981, 20, 4069-4074
62. Farr, J. L.; Abrams, M. J.; Costello, C. E.; Davison, A.; Lippard, S. J.; Jones, A. G. Organometallics 1985, 4, 139-142
63. Ojo, W.-S.; Paugam, E.; Petillon, F. Y.; Schollhammer, P.; Talarmin, J.; Muir, K. W. Organometallics 2006, 25, 4009-4018
64. Ojo, W.-S.; Petillon, F. Y.; Schollhammer, P.; Talarmin, J. Organometallics 2008, 27, 4207-4222
65. Cheng, Y.-n.; Duan, Z.; Yu, L.; Li, Z.; Zhu, Y.; Wu, Y. Org. Lett. 2008, 10, 901-904
66. Christofides, A. J. Organomet. Chem. 1983, 259, 355-365
67. North, M. Nitriles: General Methods and Aliphatic Nitriles. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Pergamon: Cambridge, 1995; Vol. 3, pp 611-640.
68. Enthaler, S. Chem.-Eur. J. 2011, 17, 9316-9319
69. Enthaler, S. Eur. J. Org. Chem. 2011, 2011, 4760-4763
70. Enthaler, S.; Weidauer, M. Catal. Lett. 2011, 141, 1079-1085
71. Hanada, S.; Motoyama, Y.; Nagashima, H. Eur. J. Org. Chem. 2008, 4097-4100
72. Ishihara, K.; Furuya, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2002, 41, 2983-2986
73. Maffioli, S. I.; Marzorati, E.; Marazzi, A. Org. Lett. 2005, 7, 5237-5239
74. Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505-5512
75. Wu, G.; Rheingold, A. L.; Heck, R. F. Organometallics 1986, 5, 1922-1924
76. Ryabov, A. D.; Van, E. R.; Le, B. G.; Pfeffer, M. Organometallics 1993, 12, 1386-1393
77. de Vaal, P.; Dedieu, A. J. Organomet. Chem. 1994, 478, 121-129
78. Vicente, J.; Abad, J. A.; López-Serrano, J.; Jones, P. G.; Nájera, C.; Botella-Segura, L. Organometallics 2005, 24, 5044-5057
79. Kolossváry, I.; Guida, W. C. J. Am. Chem. Soc. 1993, 115, 2107-2119
80. Hendrickson, J. B. J. Am. Chem. Soc. 1964, 86, 4854-4866
81. Kelly, A. E.; MacGregor, S. A.; Willis, A. C.; Nelson, J. H.; Wenger, E. Inorg. Chim. Acta 2003, 352, 79-97
82. Spencer, J.; Pfeffer, M.; DeCian, A.; Fischer, J. J. Org. Chem. 1995, 60, 1005-1012
83. Reddy, K. R.; Surekha, K.; Lee, G.-H.; Peng, S.-M.; Liu, S.-T. Organometallics 2001, 20, 5557-5563
84. Vicente, J.; Abad, J. A.; Förtsch, W.; Jones, P. G.; Fischer, A. K. Organometallics 2001, 20, 2704-2715
85. Vicente, J.; Abad, J. A.; Frankland, A. D.; López-Serrano, J.; Ramírez de Arellano, M. C.; Jones, P. G. Organometallics 2002, 21, 272-282
86. Vicente, J.; Abad, J. A.; Martínez-Viviente, E.; Jones, P. G. Organometallics 2002, 21, 4454-4467
87. Vicente, J.; Chicote, M. T.; Martínez-Martínez, A. J.; Bautista, D. Organometallics 2009, 28, 5915-5924
88. Usón, R.; Forniés, J.; Espinet, P.; Lalinde, E.; Jones, P. G.; Sheldrick, G. M. J. Organomet. Chem. 1985, 288, 249-259