Novel palladium-aminocarbene species derived from metal-mediated coupling of isonitriles and 1,3-diiminoisoindoline: Synthesis and catalytic application in Suzuki-Miyaura cross-coupling

Organometallics

Volumn 31, Issue 6, 2012, Pages 2379-2387

  Chay, Rogério S ^a   Luzyanin, Konstantin V ^a,b   Kukushkin, Vadim Yu ^b,c   Guedes Da Silva, M Fátima C ^a,d   Pombeiro, Armando J L ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^c INSTITUTE OF MACROMOLECULAR COMPOUNDS   (Russian Federation)

^d UNIVERSIDADE LUSÓFONA DE HUMANIDADES E TECNOLOGIAS   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO CARBENE COMPLEXES; ARYL HALIDES; CARBENES; CATALYTIC APPLICATIONS; CATALYTIC PROPERTIES; CYCLOHEXYL; ISOLATED YIELD; ISONITRILES; METAL-MEDIATED COUPLING; PHENYLBORONIC ACIDS; SUZUKI-MIYAURA CROSS-COUPLING;

CESIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

PALLADIUM;

EID: 84859132464     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300020j     Document Type: Article

References (62)

1. Vignolle, J.; Catton, X.; Bourissou, D. Chem. Rev. 2009, 109, 3333-3384
2. Michelin, R. A.; Pombeiro, A. J. L.; Guedes da Silva, M. F. C. Coord. Chem. Rev. 2001, 218, 75-112
3. Alder, R. W.; Allen, P. R.; Murray, M.; Orpen, A. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1121-1123
4. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309
5. Arnold, P.; Pearson, S. Coord. Chem. Rev. 2007, 251, 596-609
6. Glorius, F. Top. Organomet. Chem. 2007, 21, 1-20
7. Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612-3676
8. Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122-3172
9. Hahn, F. E.; Langenhahn, V.; Lügger, T.; Fehlhammer, W. P. Chem.-Eur. J. 2003, 9, 704-712
10. Hahn, F. E.; Langenhahn, V.; Lügger, T.; Pape, T.; Van, D. L. Angew. Chem., Int. Ed. 2005, 3759-3763
11. Hahn, F. E.; Langenhahn, V.; Pape, T. Chem. Commun. 2005, 5390-5392
12. Hahn, F. E.; Plumed, C. G.; Münder, M.; Lügger, T. Chem.-Eur. J. 2004, 10, 6285-6293
13. Rosen, E. L.; Sanderson, M. D.; Saravanakumar, S.; Bielawski, C. W. Organometallics 2007, 26, 5774-5777
14. Frey, G. D.; Herdtweck, E.; Herrmann, W. A. J. Organomet. Chem. 2006, 691, 2465-2478
15. Herrmann, W. A.; Öfele, K.; Preysing, D. V.; Herdtweck, E. J. Organomet. Chem. 2003, 684, 235-248
16. Denk, K.; Sirsch, P.; Herrmann, W. A. J. Organomet. Chem. 2002, 649, 219-224
17. Frey, G. D.; Herrmann, W. A. J. Organomet. Chem. 2005, 690, 5876-5880
18. Wanniarachchi, Y. A.; Kogiso, Yu.; Slaughter, L. M. Organometallics 2008, 27, 21-24
19. Wanniarachchi, Y. A.; Slaughter, L. M. Organometallics 2008, 27, 1055-1062
20. Wanniarachchi, Y. A.; Subramanium, S. S.; Slaughter, L. M. J. Organomet. Chem. 2009, 694, 3297-3305
21. Rosen, E. L.; Sung, D. H.; Chen, Z.; Lynch, V.; Bielawski, C. W. Organometallics 2010, 29, 250-256
22. Ruiz, J.; Perandondes, B. F. Organometallics 2009, 28, 830-836
23. Collins, M. S.; Rosen, E. L.; Lynch, V. M.; Bielawski, C. W. Organometallics 2010, 29, 3047-3053
24. Droge, T.; Wanniarachchi, Y. A.; Slaughter, L. M. Chem. Commun. 2007, 3294-3296
25. Kremzow, D.; Seidel, G.; Lehmann, C. W.; Furstner, A. Chem.-Eur. J. 2005, 11, 1833-1853
26. Dhudshia, B.; Thadani, A. N. Chem. Commun. 2006, 6, 668-670
27. Tskhovrebov, A. G.; Luzyanin, K. V.; Kuznetsov, M. L.; Sorokoumov, V. N.; Balova, I. A.; Haukka, M.; Kukushkin, V. Yu. Organometallics 2011, 30, 863-874
28. Luzyanin, K. V.; Tskhovrebov, A. G.; Carias, M. C.; Guedes da Silva, M. F. C.; Pombeiro, A. J. L.; Kukushkin, V. Yu. Organometallics 2009, 28, 6559-6566
29. Slaughter, L. M. Comm. Inorg. Chem. 2008, 29, 46-72
30. Moncada, A. I.; Khanb, M. A.; Slaughter, L. M. Tetrahedron Lett. 2005, 46, 1399-1403
31. Moncada, A. I.; Manne, S.; Tanski, J. M.; Slaughter, L. M. Organometallics 2006, 25, 491-505
32. Bartolomé, C.; Ramiro, Z.; Pérez-Galán, P.; Bour, C.; Raducan, M.; Echavarren, A. M.; Espinet, P. Inorg. Chem. 2008, 47, 11391-11397
33. Bartolomé, C.; Ramiro, Z.; García-Cuadrado, D.; Pérez-Galán, P.; Raducan, M.; Bour, C.; Echavarren, A. M.; Espinet, P. Organometallics 2010, 29, 951-956
34. Bartolomé, C.; García-Cuadrado, D.; Ramiro, Z.; Espinet, P. Organometallics 2010, 29, 3589-3592
35. Bartolomé, C.; García-Cuadrado, D.; Ramiro, Z.; Espinet, P. Inorg. Chem. 2010, 49, 9758-9764
36. Hashmi, A. S. K.; Hengst, T.; Lothschütz, C.; Rominger, F. Adv. Synth. Catal. 2010, 352, 1315-1337
37. Seo, H.; Roberts, B. P.; Abboud, K. A.; Merz, K. A., Jr.; Hong, S. Org. Lett. 2010, 12, 4860-4863
38. Seo, H.; Snead, D. R.; Abboud, K. A.; Hong, S. Organometallics 2011, 30, 5725-5730
39. Hashmi, A. S. K.; Haffner, T.; Rudolph, M.; Rominger, F. Eur. J. Org. Chem. 2011, 667-671
40. Hashmi, A. S. K.; Haffner, T.; Rudolph, M.; Rominger, F. Chem.-Eur. J. 2011, 17, 8195-8201
41. Handa, S.; Slaughter, L. M. Angew. Chem., Int. Ed. 2012, in press (DOI: 10.1002/anie.201107789).
42. Luzyanin, K. V.; Pombeiro, A. J. L.; Haukka, M.; Kukushkin, V. Yu. Organometallics 2008, 27, 5379-5389
43. Luzyanin, K. V.; Guedes da Silva, M. F. C.; Kukushkin, V. Yu.; Pombeiro, A. J. L. Inorg. Chim. Acta 2009, 362, 833-838
44. Luzyanin, K. V.; Tskhovrebov, A. G.; Guedes da Silva, M. F. C.; Haukka, M.; Pombeiro, A. J. L.; Kukushkin, V. Yu. Chem.-Eur. J 2009, 15, 5969-5978
45. Elvidge, J. A.; Linstead, R. P. J. Chem. Soc. 1952, 5000-5007
46. Zhang, Zh.-Q.; Njus, J. M.; Sandman, D. J.; Guo, C.; Foxman, B. M.; Erk, P.; van Gelder, R. Chem. Commun. 2004, 886-887
47. Lyubimtsev, A. V.; Barański, A.; Isayaikin, M. K.; Smirnov, R. P. Chem. Heterocycl. Cmpd. 1997, 33, 937-941
48. Acker, A.; Hofmann, H.-J.; Cimiraglia, R. J. Mol. Struct. (THEOCHEM) 1994, 315, 43-51
49. Bertani, R.; Mozzon, M.; Michelin, R. A. Inorg. Chem. 1988, 27, 2809-2815
50. 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
51. Bonati, F.; Minghetti, G. J. Organomet. Chem. 1970, 24, 251-256
52. Michelin, R. A.; Zanotto, L.; Braga, D.; Sabatino, P.; Angelici, R. J. Inorg. Chem. 1988, 27, 85-92
53. Crociani, B.; Boschi, T.; Belluco, U. Inorg. Chem. 1970, 9, 2021-2025
54. Domiano, P.; Musatti, A.; Nardelli, M.; Predieri, G. J. Chem. Soc., Dalton Trans. 1975, 2165-2168
55. Chay, R. S.; Luzyanin, K. V. Inorg. Chim. Acta 2012, 380, 322-327
56. Bruker APEX2 & SAINT; Bruker, AXS Inc.: Madison, WI, USA, 2004.
57. Sheldrick, G. M. SADABS, Bruker Nonius scaling and absorption correction, v 2.10; Bruker AXS, Inc.: Madison, WI, USA, 2003.
58. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Determination; University of Göttingen: Göttingen, Germany, 1997.
59. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
60. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838
61. Spek, A. L. PLATON/SQUEEZE, An effective tool for taking the contribution of disordered solvent into account in crystal structure refinement In Bijvoet Center for Biomolecular Research; Utrecht University: Padualaan 8, 3584 CH Utrecht, The Netherlands, 2005.
62. Moncada, A. I.; Tanski, J. M.; Slaughter, L. M. J. Organomet. Chem. 2005, 690, 6247-6251