Novel reactivity mode of metal diaminocarbenes: Palladium(II)-mediated coupling between acyclic diaminocarbenes and isonitriles leading to dinuclear species

Organometallics

Volumn 30, Issue 12, 2011, Pages 3362-3370

  Tskhovrebov, Alexander G ^a   Luzyanin, Konstantin V ^a,b   Dolgushin, Fedor M ^c   Guedes Da Silva, M Fátima C ^b,d   Pombeiro, Armando J L ^b   Kukushkin, Vadim Yu ^a,e  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^d UNIVERSIDADE LUSÓFONA DE HUMANIDADES E TECNOLOGIAS   (Portugal)

^e INSTITUTE OF MACROMOLECULAR COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

2-AMINOPYRIDINE; ACYCLIC DIAMINOCARBENES; AMINO GROUP; CARBENES; CASCADE REACTIONS; CYCLOHEXYL; DIAMINOCARBENES; DINUCLEAR COMPLEX; DINUCLEAR SPECIES; EQUIMOLAR AMOUNT; HIGH RESOLUTION; ISOLATED YIELD; ISONITRILES; METAL-MEDIATED COUPLING; MOLAR RATIO; NEUTRAL SPECIES; REACTION MIXTURE; RING-CLOSURE; SINGLE CRYSTAL X-RAY DIFFRACTION;

HEATING; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS; X RAY DIFFRACTION;

PALLADIUM;

EID: 79959434032     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om2002574     Document Type: Article

References (65)

1. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309
2. Arnold, P.; Pearson, S. Coord. Chem. Rev. 2007, 251, 596-609
3. Liddle, S. T.; Edworthy, I. S.; Arnold, P. L. Chem. Soc. Rev. 2007, 36, 1732-1744
4. Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122-3172
5. Schuster, O.; Yang, L.; Raubenheimer, H. G.; Albrecht, M. Chem. Rev. 2009, 109, 3445-3478
6. Vignolle, J.; Catton, X.; Bourissou, D. Chem. Rev. 2009, 109, 3333-3384
7. Cesar, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619-636
8. Glorius, F. Top. Organomet. Chem. 2007, 21, 1-20
9. Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440-1449
10. Díez-Gonzaález, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612-3676
11. Michelin, R. A.; Pombeiro, A. J. L.; Guedes da Silva, M. F. C. Coord. Chem. Rev. 2001, 218, 75-112
12. Alder, R. W.; Allen, P. R.; Murray, M.; Orpen, A. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1121-1123
13. Herrmann, W. A.; Öfele, K.; Preysing, D. V.; Herdtweck, E. J. Organomet. Chem. 2003, 684, 235-248
14. Frey, G. D.; Herrmann, W. A. J. Organomet. Chem. 2005, 690, 5876-5880
15. Frey, G. D.; Herdtweck, E.; Herrmann, W. A. J. Organomet. Chem. 2006, 691, 2465-2478
16. Rosen, E. L.; Sanderson, M. D.; Saravanakumar, S.; Bielawski, C. W. Organometallics 2007, 26, 5774-5777
17. Droge, T.; Wanniarachchi, Y. A.; Slaughter, L. M. Chem. Commun. 2007, 3294-3296
18. Wanniarachchi, Y. A.; Kogiso, Yu.; Slaughter, L. M. Organometallics 2008, 27, 21-24
19. Wanniarachchi, Y. A.; Subramanium, S. S.; Slaughter, L. M. J. Organomet. Chem. 2009, 694, 3297-3305
20. Wanniarachchi, Y. A.; Slaughter, L. M. Organometallics 2008, 27, 1055-1062
21. Ruiz, J.; Perandondes, B. F. Organometallics 2009, 28, 830-836
22. Rosen, E. L.; Sung, D. H.; Chen, Z.; Lynch, V.; Bielawski, C. W. Organometallics 2010, 29, 250-256
23. Collins, M. S.; Rosen, E. L.; Lynch, V. M.; Bielawski, C. W. Organometallics 2010, 29, 3047-3053
24. Nolan, S. P.; Navarro, O. In Comprehensive Organometallic Chemistry III; Canty, A., Ed.; Elsevier: Oxford, 2007; pp 1-38, and references therein.
25. Tschugajeff(Chugaev), L.; Skanawy-Grigorjewa, M. J. Russ. Chem. Soc. 1915, 47, 776
26. Badley, E. M.; Chatt, J.; Richards, R. L. J. Chem. Soc. A 1971, 1-21
27. Balch, A. L.; Parks, J. E. J. Am. Chem. Soc. 1974, 96, 4114-4121
28. Zanotto, L.; Bertani, R.; Michelin, R. A. Inorg. Chem. 1990, 29, 3265-3268
29. Bertani, R.; Mozzon, M.; Michelin, R. A.; Benetollo, F.; Bombieri, G.; Castilho, T. J.; Pombeiro, A. J. L. Inorg. Chim. Acta 1991, 189, 175-187
30. Wang, Y.; Pombeiro, A. J. L.; Michelin, R. A.; Mozzon, M.; Bertani, R. Bull. Pol. Acad. Sci., Chem. 1994, 42, 307-321
31. Slaughter, L. M. Comm. Inorg. Chem. 2008, 29, 46-72
32. Pombeiro, A. J. L.; Guedes da Silva, M. F. C.; Michelin, R. A. Coord. Chem. Rev. 2001, 218, 43-74
33. Kukushkin, V. Yu.; Pombeiro, A. J. L. Chem. Rev. 2002, 102, 1771-1802
34. Kukushkin, V. Yu.; Pombeiro, A. J. L. Inorg. Chim. Acta 2005, 358, 1-21
35. Pombeiro, A. J. L.; Kukushkin, V. Y. In Comprehensive Coordination Chemistry; Elsevier, 2004; p 639.
36. Bokach, N. A.; Kukushkin, V. Y. Russ. Chem. Bull. 2006, 55, 1869-1882
37. Bokach, N. A.; Kukushkin, V. Y. Usp. Khim. 2005, 74, 164-182
38. Luzyanin, K. V.; Guedes da Silva, M. F. C.; Kukushkin, V. Yu.; Pombeiro, A. J. L. Inorg. Chim. Acta 2009, 362, 833-888
39. Luzyanin, K. V.; Pombeiro, A. J. L.; Haukka, M.; Kukushkin, V. Y. Organometallics 2008, 27, 5379-5389
40. Kopylovich, M. N.; Kukushkin, V. Yu.; Haukka, M.; Luzyanin, K. V.; Pombeiro, A. J. L. J. Am. Chem. Soc. 2004, 126, 15040-15041
41. Luzyanin, K. V.; Kukushkin, V. Yu.; Kopylovich, M. N.; Nazarov, A. A.; Galanski, M.; Pombeiro, A. J. L. Adv. Synth. Catal. 2008, 350, 135-142
42. Chay, R. S.; Luzyanin, K. V.; Guedes da Silva, M. F. C.; Pombeiro, A. J. L.; Kukushkin, V. Y. Unpublished results.
43. Tskhovrebov, A. G.; Luzyanin, K. V.; Kuznetsov, M. L.; Sorokoumov, V. N.; Balova, I. A.; Haukka, M.; Kukushkin, V. Y. Organometallics 2011, 30, 863-874
44. Zanella, R.; Boschi, T.; Crociani, B.; Belluco, U. J. Organomet. Chem. 1974, 71, 135-143
45. Zanella, R.; Boschi, T.; Nicolini, M.; Belluco, U. J. Organomet. Chem. 1973, 49, C91-C94
46. Boschi, T.; Crociani, B.; Nicolini, M.; Belluco, U. Inorg. Chim. Acta 1975, 12, 39-44
47. Tapu, D.; Dixon, D. A.; Roe, C. Chem. Rev. 2009, 109, 3385-3407
48. Domiano, P.; Musatti, A.; Nardelli, M.; Predieri, G. J. Chem. Soc., Dalton Trans. 1975, 2165-2168
49. Moncada, A. I.; Manne, S.; Tanski, J. M.; Slaughter, L. M. Organometallics 2006, 25, 491-505
50. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A.; G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1-S19
51. Kitano, Y.; Hori, T. Acta Crystallogr. B 1981, 37, 1919-1921
52. Perreaul, D.; Drouin, M.; Michel, A.; Harvey, P. D. Inorg. Chem. 1993, 32, 1903-1912
53. Drouin, M.; Perreaul, D.; Harvey, P. D.; Michel, A. Acta Crystallogr. C 1991, 47, 752-754
54. Paul, F.; Fischer, J.; Ochsenbein, P.; Osborn, J. A. Angew. Chem., Int. Ed. 1993, 32, 1638-1640
55. Vicente, J.; Abad, J.-A.; Frankland, A. D.; Lopez-Serrano, J.; De Arellano, M. C. R.; Jones, P. G. Organometallics 2002, 21, 272-282
56. Baidina, I. A.; Podberezskaya, N. V.; Krylova, L. F.; Borisov, S. V.; Bakakin, V. V. Zh. Strukt. Khim. (Russ. J. Struct. Chem.) 1980, 21, 106-110
57. Barefield, E. K.; Carrier, A. M.; Sepelak, D. J.; Van Derveer, D. G. Organometallics 1982, 1, 103-110
58. Bonati, F.; Minghetti, G. J. Organomet. Chem. 1970, 24, 251-256
59. Michelin, R. A.; Zanotto, L.; Braga, D.; Sabatino, P.; Angelici, R. J. Inorg. Chem. 1988, 27, 85-92
60. Michelin, R. A.; Zanotto, L.; Braga, D.; Sabatino, P.; Angelici, R. J. Inorg. Chem. 1988, 27, 93-99
61. APEX II & SAINT software package; Bruker AXS Inc., 2005.
62. Sheldrick, G. M. Acta Crystallogr. Sect. A 2008, A64, 112-122
63. Sheldrick, G. M. SADABS, Bruker Nonius scaling and absorption correction; 2001, 8.
64. Sheldrick, G. M. Acta Crystallogr. Sect. A 1990, 46, 467-473
65. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838