Insertion of isocyanides across the Pd-C bond of phosphinoquinoline allyl palladium complexes bearing η1- and η3-coordinated allyl groups. A synthetic and mechanistic study

Organometallics

Volumn 33, Issue 7, 2014, Pages 1700-1709

  Canovese, L ^a   Visentin, F ^a   Santo, C ^a   Bertolasi, V ^b  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; CYANIDES; EQUILIBRIUM CONSTANTS; LIGANDS;

ALLYL DERIVATIVES; FIRST-ORDER PROCESS; INSERTION PRODUCTS; MECHANISTIC STUDIES; PALLADIUM COMPLEXES; SECOND-ORDER DEPENDENCE; SOLID-STATE STRUCTURES; STRUCTURAL CHARACTERISTICS;

PALLADIUM COMPOUNDS;

EID: 84898624010     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500057h     Document Type: Article

References (107)

1. Heck, R. F. In Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
2. Tsuji, J. In Palladium Reagents and Catalysts; John Wiley; Chichester U.K., 1995.
3. Qiu, G.; Ding, Q.; Wu, J. Chem. Soc. Rev. 2013, 42, 5257-5269
4. Vlaar, T.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew. Chem., Int. Ed. 2013, 52, 7084-7097
5. Lang, S. Chem Soc. Rev. 2013, 42, 4867-4880
6. Fruchey, E. R.; Monks, B. M.; Patterson, A. M.; Cook, S. P. Org. Lett. 2013, 15, 4362-4365
7. Nanjo, T.; Yamamoto, S.; Tsukano, C.; Takemoto, Y. Org. Lett. 2013, 15, 3754-3757
8. García-López, J.-A.; Oliva-Madrid, M.-J.; Saura-Llamas, I.; Bautista, D.; Vicente, J. Chem. Commun. 2012, 48, 6744-6746
9. López, C.; Salmi, M.; Mas, A.; Piotrowski, P.; Font-Bardia, M.; Calvet, T. Eur. J. Inorg. Chem. 2012, 1702-1709
10. Vicente, J.; Saura-Llamas, I.; Turpin, J.; Bautista, D.; Ramirez de Arellano, C.; Jones, P. G. Organometallics 2009, 28, 4175-4195
11. Knorr, M.; Jourdain, I.; Braunstein, P.; Strohmann, C.; Tiripicchio, A.; Ugozzoli, F. Dalton Trans. 2006, 5248-5258
12. Vicente, J.; Abad, J.-A.; López-Serrano, J.; Jones, P. G.; Nájera, C.; Botella-Segura, L. Organometallics 2005, 24, 5044-5057
13. Canovese, L.; Visentin, F.; Chessa, G.; Uguagliati, P.; Santo, C.; Dolmella, A. Organometallics 2005, 24, 3297-3308
14. Chicote, M.-T.; Vicente-Hernández, I.; Jones, P. G.; Vicente, J. Organometallics 2012, 31, 6252-6261
15. Leone, A.; Consiglio, G. J. Organomet. Chem. 2006, 691, 4204-4214
16. Setsune, J.-i.; Yamauchi, T.; Tanikawa, S.; Hirose, Y.; Watanabe, J.-y. Organometallics 2004, 23, 6058-6065
17. Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620-1621
18. Vicente, J.; Abad, J.-A.; Fortsch, W.; López-Sáez, M. J.; Jones, P. G. Organometallics 2004, 23, 4414-4429
19. Braunstein, P.; Durand, J.; Knorr, M.; Strohmann, C. Chem. Commun. 2001, 211-212
20. Delis, J. G. P.; Aubel, P. G.; Vrieze, K.; van Leeuwen, P. W. N. M.; Veldman, N.; Speck, A. L. Organometallics 1997, 16, 4150-4160
21. García-López, J.-A.; Saura-Llama, I.; McGrady, J. E.; Bautista, D.; Vicente, J. Organometallics 2012, 31, 8333-8347
22. Vicente, J.; Abad, J. A.; López-Sáez, M.-J.; Jones, P. G. Organometallics 2010, 29, 409-416
23. Bai, T.; Xue, L.; Zhu, J.; Sung, H. H.-Y.; Ma, S.; Williams, I. D.; Lin, Z.; Jia, G. Organometallics 2008, 27, 2614-2626
24. Sirlin, C.; Chengebroyen, J.; Konrath, R.; Ebeling, G.; Raad, I.; Dupont, J.; Paschaki, M.; Kotzyba-Hibert, F.; Harf-Monteil, C.; Pfeffer, M. Eur. J. Org. Chem. 2004, 1724-1731
25. Canovese, L.; Visentin, F.; Chessa, G.; Uguagliati, P.; Santo, C.; Bandoli, G.; Maini, L. Organometallics 2003, 22, 3230-3238
26. Vicente, J.; Abad, J.-A.; Bergs, R.; Ramirez de Arellano, M. C.; Martínez-Viviente, E.; Jones, P. G. Organometallics 2000, 19, 5597-5607
27. Groen, J. H.; Delis, J. G. P.; van Leeuwen, P. W. N. M.; Vrieze, K. Organometallics 1997, 16, 68-77
28. Delis, J. G. P.; Aubel, P. G.; Vrieze, K.; van Leeuwen, P. W. N. M.; Veldman, N.; Speck, A. L. Organometallics 1997, 16, 2948-2957
29. Frutos-Pedreño, R.; Gonzáles-Herrero, P.; Vicente, J. Organometallics 2012, 31, 3361-3372
30. Vicente, J.; Saura-Llamas, I. Comments Inorg. Chem. 2007, 28, 39-72
31. Vicente, J.; Saura-Llamas, I.; Garcia-López, J.-A.; Calmuschi-Cula, B.; Bautista, D. Organometallics 2007, 26, 2768-2776
32. Vicente, J.; Abad, J.-A.; Förtsch, W.; Jones, P. G.; Fischer, A. K. Organometallics 2001, 20, 2704-2715
33. Wojcicki, A. A. Adv. Organomet. Chem. 1973, 11, 87-145
34. Kulhman, E. J.; Alexander, J. J. Coord. Chem. Rev. 1980, 33, 195-225
35. Backer, T. M.; Alexander, J. J.; Krause Bauer, J. A.; Nauss, J. L.; Wireko, F. C. Organometallics 1999, 18, 5594-5605
36. Haore, J. L.; Cavell, K. J.; Hecker, R.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1996, 2197-2205
37. Koga, N.; Morokuma, K. In Theoretical Aspects of Homogeneous Catalysis; van Leeuwen, P. W. N. M.; Morokuma, K.; van Lenthe, J. H., Eds.; Kluwer: Dordrecht, The Netherlands, 1995.
38. Calhorda, H. J.; Brown, J. M.; Cooley, N. A. Organometallics 1991, 10, 1431-1438
39. Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1996, 118, 7337-7344
40. Veya, P.; Floriani, C. Organometallics 1993, 12, 4899
41. Delis, J. G. P.; Aubel, P. G.; Vrieze, K.; van Leeuwen, P. W. N. M.; Veldman, N.; Speck, A. L.; van Neer, F. J. R. Organometallics 1997, 16, 2948-2957
42. Owen, G. R.; Vilar, R.; White, A. J. P.; Williams, D. J. Organometallics 2002, 21, 4799-4807
43. Vicente, J.; Abad, J.-A.; Martinez-Viviente, E.; Jones, P. G. Organometallics 2002, 21, 4454-4566 and references therein
44. Canovese, L.; Visentin, F.; Santo, C.; Levi, C.; Dolmella, A. Organometallics 2007, 26, 5590-5601
45. Dupont, J.; Pffefer, M.; Daran, J. C.; Jeannin, Y. Organometallics 1987, 6, 899-901
46. Zografidis, A.; Polborn, K.; Beck, W.; Markies, B. A.; van Koten, G. Z. Naturforsch., B: Chem. Sci 1994, 49, 1494-1498
47. Yamamoto, A. Bull. Chem. Soc. Jpn. 1995, 68, 433-446
48. Kayaki, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1997, 70, 917-927
49. Vicente, J.; Abad, J. A.; Shaw, K. F.; Gil-Rubio, J.; Ramirez de Arellano, M. C.; Jones, P. G. Organometallics 1997, 16, 4557-4566
50. Böhm, A.; Polborn, K.; Sünkel, K.; Beck, W. Z. Naturforsch., B: Chem. Sci. 1998, 53, 448-458
51. Lin, Y.-S.; Yamamoto, A. Organometallics 1998, 17, 3466-3478
52. Vicente, J.; Saura-Llamas, I.; Turpin, J.; Ramirez de Arellano, M. C.; Jones, P. G. Organometallics 1999, 18, 2683-2693
53. Yamamoto, A. J. Chem. Soc., Dalton Trans. 1999, 1027-1038
54. Saluste, C. G.; Whitby, R. J.; Furber, M. Angew. Chem., Int. Ed. 2000, 39, 4156-4158
55. Vicente, J.; Abad, J. A.; Frankland, A. D.; Lopez-Serrano, J.; Ramirez de Arellano, M. C.; Jones, P. G. Organometallics 2002, 21, 272-282
56. Onitsuka, K.; Yamamoto, M.; Suzuki, S.; Takahashi, S. Organometallics 2002, 21, 581-583
57. Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215-3218
58. Kim, Y. J.; Chang, X. H.; Han, J. T.; Lim, M. S.; Lee, S. W. Dalton Trans. 2004, 3699-3708
59. Albert, J.; D'Andrea, L.; Granell, J.; Zafrilla, J.; Font-Bardia, M.; Solans, X. J. Organomet. Chem. 2007, 692, 4895-4902
60. Bortoluzzi, M.; Paolucci, G.; Pitteri, B.; Vavasori, A.; Bertolasi, V. Organometallics 2009, 28, 3247-3255
61. Canovese, L.; Visentin, F.; Santo, C.; Levi, C. Organometallics 2009, 28, 6762-6770
62. Canovese, L.; Visentin, F.; Chessa, G.; Santo, C.; Uguagliati, P.; Bandoli, G. J. Organomet. Chem. 2002, 650, 43 and references therein (for structural comparison entry code HUGGAR).
63. Canovese, L.; Visentin, F.; Chessa, G.; Uguagliati, P.; Bandoli, G. Organometallics 2000, 19, 1461-1463
64. Delis, J. G. P.; Aubel, P. G.; van Leeuwen, P. W. N. M.; Vrieze, K.; Veldman, N.; Speck, A. L. J. Chem. Soc., Chem. Commun. 1995, 2233
65. Kajimoto, T.; Takahashi, H.; Tsuji, J. J. Organomet. Chem. 1970, 23, 275-280
66. Boschi, T.; Crociani, B. Inorg. Chim. Acta 1971, 5, 477-480
67. Scrivanti, A.; Carturan, G.; Crociani, B. Organometallics 1983, 2, 1612-1617
68. Jutand, A. App. Organomet. Chem. 2004, 18, 574-582 and references therein
69. Garcia-Iglesias, M.; Buñuel, E.; Cárdenas, D. J. Organometallics 2006, 25, 3611-3618 and references therein
70. Aydin, J.; Szabó, K. J. Org. Lett. 2008, 10, 2881-2884 and references therein
71. Cucciolito, M. E.; Vitagliano, A. Organometallics 2008, 27, 6360-6363
72. Canovese, L.; Visentin, F.; Santo, C.; Chessa, G.; Bertolasi, V. Organometallics 2010, 29, 3027-3038 and references therein
73. Canovese, L.; Chessa, G.; Santo, C.; Visentin, F.; Uguagliati, P. Inorg. Chim. Acta 2003, 346, 158-168
74. Delley, B. J. Chem. Phys. 1990, 92, 508-517
75. Delley, B. J. Chem. Phys. 2000, 113, 7756-7764
76. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865-3868
77. Delley, B. J. Phys. Chem. A 2006, 110, 13632-13639
78. Delley, B. Phys. Rev. B 2002, 66, 155125/1-155125/9
79. Klamt, A.; Schürmann, G. J. Chem. Soc., Perkin Trans. 1993, 2, 799-805
80. Delley, B. Mol. Simul. 2006, 32, 117-123
81. Kayaki, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1997, 70, 917-927
82. Yamamoto, Y.; Yamazaki, H. Coord. Chem. Rev. 1972, 8, 225-239
83. Treichel, P. M. Adv. Organomet. Chem. 1973, 11, 21-86
84. Singleton, E.; Ootsthuizen, H. E. Adv. Organomet. Chem. 1983, 22, 209-310
85. Onitsuka, K.; Yanai, K.; Takei, F.; Ioh, T.; Takahashi, S. Organometallics 1994, 13, 3862-3867
86. Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1996, 118, 7337-7344
87. Yamamoto, Y.; Yamzaki, H. Bull. Chem. Soc. Jpn. 1970, 43, 2653
88. Yamamoto, Y.; Yamzaki, H. Bull. Chem. Soc. Jpn. 1970, 43, 3634
89. Yamamoto, Y.; Yamzaki, H. Inorg. Chem. 1974, 13, 438-443
90. Tanase, T.; Ohizumi, T.; Kobayashi, K.; Yamamoto, Y. Organometallics 1996, 15, 3404-34011
91. Yamamoto, Y.; Tanase, T.; Yanai, T.; Asano, T.; Kobayashi, K. J. Organomet. Chem. 1993, 456, 287-291
92. Onitsuka, K.; Joh, T.; Takahashi, S. J. Organomet. Chem. 1994, 464, 247-251
93. Ito, Y.; Ihara, E.; Murakami, M. J. Am. Chem. Soc. 1990, 112, 6446-6447
94. Macchioni, A.; Zuccaccia, C.; Clot, E.; Gruet, K.; Crabtree, R. H. Organometallics 2001, 20, 2367-2373
95. Crociani, B.; Antonaroli, S.; Paci, M.; Di Bianca, F.; Canovese, L. Organometallics 1997, 16, 384-391
96. Burnett, M. N.; Johnson, C. K. ORTEP III, Report ORNL-6895; Oak Ridge National Laboratory: Oak Ridge, TN, 1996.
97. Rülke, R. E.; Kaasjager, V. E.; Wehman, P.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Fraanje, J.; Goubitz, K.; Spek, A. Organometallics 1996, 15, 3022-3031
98. Giannoccaro, P.; Cornacchia, D.; Doronzo, S.; Mesto, E.; Quaranta, E.; Aresta, M. Organometallics 2006, 25, 2872-2879
99. Canovese, L.; Visentin, F.; Chessa, G.; Santo, C.; Dolmella, A. Dalton Trans. 2009, 475-9485
100. Wheman, P.; van Donge, H. M.A.; Hagos, A.; Kamer, P. C. J. Organomet. Chem. 1997, 535, 183-193
101. Hartley, F. R.; Jones, S. R. J. Organomet. Chem. 1974, 66, 465-473
102. Otwinowski, Z.; Minor, W. In Methods in Enzymology; Carter, C. W.; Sweet, R. M. Eds.; Academic Press: London, 1997; Vol. 276, Part A, pp 307-326.
103. Blessing, R. H. Acta Crystallogr., Sect. A 1995, 51, 33-38
104. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119
105. Sheldrick, G. M. SHELX-97, Program for Crystal Structure Refinement; University of Gottingen: Germany, 1997.
106. Nardelli, M. J. Appl. Crystallogr. 1995, 28, 659-659
107. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838