Application of chiral amine-imine ligands in palladium-catalyzed polyketone synthesis: effect of ligand backbone on the polymer stereochemistry

Organometallics

Volumn 28, Issue 15, 2009, Pages 4464-4474

  Axet, M Rosa ^a   Amoroso, Francesco ^a   Bottari, Giovanni ^b   D'Amora, Angela ^a   Zangrando, Ennio ^a   Faraone, Felice ^b   Drommi, Dario ^b   Saporita, Maria ^b   Carfagna, Carla ^c   Natanti, Paolo ^c   Seraglia, Roberta ^d   Milani, Barbara ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

^c UNIVERSITY OF URBINO   (Italy)

^d CNR Consiglio Nazionale delle Ricerche   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ATOMS; CATALYST ACTIVITY; CHELATION; COPOLYMERIZATION; KETONES; NITROGEN; PALLADIUM; PALLADIUM COMPOUNDS; POLYMERS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ATACTIC; BINAPHTHALENES; BINAPHTHYL MOIETY; BUILDING BLOCKES; CHIRAL AMINES; COPOLYMERIZATION REACTIONS; END-GROUPS; IMINE LIGANDS; ISOTACTICS; MALDI-TOF; NITROGEN ATOM; NITROGEN-DONOR LIGANDS; PALLADIUM COMPLEXES; POLYKETONES; POLYMERIC CHAIN; REACTION MIXTURE;

LIGANDS;

EID: 84908659797     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900300w     Document Type: Article

References (62)

1. Coates, G. W.; Hustad, P. D.; Reinartz, S. Angew. Chem., Int. Ed. 2002, 41, 2236-2257.
2. Coates, G. W. J. Chem. Soc, Dalton Trans. 2002, 467-475.
3. Domski, G. J.; Rose, J. M.; Coates, G. W.; Bolig, A. D.; Brookhart, M. Prog. Polym. Sci. 2007, 32, 30-92.
4. Busico, V. Macromol. Chem. Phys. 2007, 208, 26-29.
5. Drent, E.; Budzelaar, P. H. M. Chem. Rev. 1996, 96, 663-681.
6. Bianchini, C.; Meli, A. Coord. Chem. Rev. 2002, 225, 35-66.
7. Nakano, K.; Kosaka, N.; Hiyama, T.; Nozaki, K. Dalton Trans. 2003, 4039-4050.
8. Durand, J.; Milani, B. Coord. Chem. Rev. 2006, 250, 542-560.
9. Suárez, E. J. G.; Godard, C.; Ruiz, A.; Claver, C. Eur. J. Inorg. Chem. 2007, 2582-2593.
10. Anselment, T. M. J.; Vagin, S. I.; Rieger, B. Dalton Trans. 2008, 4537-548.
11. Scarel, A.; Axet, M. R.; Amoroso, F.; Ragaini, F.; Elsevier, C. J.; Holuigue, A.; Carfagna, C.; Mosca, L.; Milani, B. Organometallics 2008, 27, 1486-1494.
12. Villagra, D.; Lopez, R.; Moya, S. A.; Claver, C.; Bastero, A. Organometallics 2008, 27, 1019-1021.
13. Bianchini, C.; Meli, A.; Oberhauser,W.; Segarra, A. M.; Passaglia, E.; Lamac, M.; Stepnicka, P. Eur. J. Inorg. Chem. 2008, 441-452.
14. Flapper, J.; Reek, J. N. H. Angew. Chem., Int. Ed. 2007, 46, 85908592.
15. Bianchini, C.; Meli, A.; Oberhauser, W.; Claver, C.; Garcia Suarez, E. J. Eur. J. Inorg. Chem. 2007, 2702-2710.
16. Malinova, V.; Rieger, B. Biomacromolecules 2006, 7, 2931-2936.
17. Benito, J. M.; de Jesus, E.; de la Mata, F. J.; Flores, J. C.; Gomez, R. Organometallies 2006, 25, 3045-3055.
18. Durand, J.; Scarel, A.; Milani, B.; Seraglia, R.; Gladiali, S.; Carfagna, C.; Binotti, B. Helv. Chim. Acta 2006, 89, 1752-1771.
19. Beckerle, K.; Manivannan, R.; Lian, B.; Meppelder, G.-Jan M.; Raabe, G.; Spaniol, Thomas, P.; Ebeling, H.; Pelascini, F.; Mulhaupt, R.; Okuda, J. Angew. Chem., Int. Ed. 2007, 46,4790-4793.
20. Carpentier, J.-F. Angew. Chem., Int. Ed. 2007, 46, 6404-6406.
21. Nozaki, K. Synthesis of chiral, optically active copolymers. In Catalytic Synthesis of Alkene-Carbon Monoxide Copolymers and Cooligomers; Sen, A., Ed.; Kluwer Academic Publishers: Dordrecht, 2003; pp 217-235.
22. Brookhart, M.;Wagner, M. I.; Balavoine, G. G. A.; Haddou, H. A. J. Am. Chem. Soc. 1994, 116, 3641-3642.
23. Bartolini, S.; Carfagna, C.; Musco, A. Macromol. Rapid Commun. 1995, 16, 9-14.
24. Nozaki, K.; Sato, N.; Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911-9912.
25. Consiglio, G.; Milani, B., Stereochemical aspects of cooligomerization and copolymerization; In Catalytic Synthesis of Alkene-Carbon Monoxide Copolymers and Cooligomers; Sen, A., Ed.; Kluwer Academic Publishers: Dordrecht, 2003; pp 189-215.
26. Sperrle, M.; Aeby, A.; Consiglio, G.; Pfaltz, A. HeIv. Chim. Acta 1996, 79, 1387-1392.
27. Bastero, A.; Ruiz, A.; Claver, C.; Castillón, S. Eur. J. Inorg. Chem. 2001, 3009-3011.
28. Bastero, A.; Claver, C.; Ruiz, A.; Castillon, S.; Daura, E.; Bo, C.; Zangrando, E. Chem. Eur. J. 2004, 10, 3747-3760.
29. Noyori, R.; Takaya, H. Ace Chem. Res. 1990, 23, 345-350.
30. Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 31553212.
31. Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hijama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779-12795.
32. Nozaki, K.; Komaki, H.; Kawashima, Y.; Hiyama, T.; Matsubara, T. J. Am. Chem. Soc. 2001, 123, 534-544.
33. Iggo, J. A.; Kawashima, Y.; Liu, J.; Hiyama, T.; Nozaki, K. Organometallics 2003, 22, 5418-5422.
34. Reetz, M. T.; Aderlein, G.; Angermund, K. J. Am. Chem. Soc. 2000, 122, 996-997.
35. Gsponer, A.; Consiglio, G. HeIv. Chim. Acta 2003, 86, 21702172.
36. Sirbu, D.; Consiglio, G.; Milani, B.; Kumar, P. G. A.; Pregosin, P. S.; Gischig, S. J. Organomet. Chem. 2005, 690, 2254-2262.
37. Leone, A.; Consiglio, G. HeIv. Chim. Acta 2006, 89, 2720-2727.
38. Drommi, D.; Saporita, M.; Bruno, G.; Faraone, F.; Scafato, P.; Rosini, C. Dalton Trans. 2007, 1509-1519.
39. Brancatelli, G.; Saporita, M.; Drommi, D.; Nicolò, F.; Faraone, F. J. Organomet. Chem. 2007, 692, 5598-5604.
40. Saporita, M.; Bottari, G.; Brancatelli, G.; Drommi, D.; Bruno, G.; Faraone, F. Eur. J. Inorg. Chem. 2008, 59-72.
41. Rülke, R. E.; Ernsting, J. M.; Spek, A. L.; Elsevier, C. J.; Van Leeuwen, P. W. N. M.; Vrieze, K. Inorg. Chem. 1993, 32, 5769-5778.
42. Groen, J. H.; Delis, J. G. P.; vanLeeuwen, P.; Vrieze, K. Organometallics 1997, 16, 68-77.
43. Milani, B.; Marson, A.; Zangrando, E.; Mestroni, G.; Ernsting, J. M.; Elsevier, C. J. Inorg. Chim. Acta 2002, 327, 188-201.
44. Widhalm, M.; Nettekoven, U.; Kalchhauser, H.; Mereiter, K.; Calhorda, M. J.; Felix, V. Organometallies 2002, 21, 315.
45. Bastero, A.; Ruiz, A.; Claver, C.; Milani, B.; Zangrando, E. Organometallies 2002, 21, 5820-5829.
46. Scarel, A.; Durand, J.; Franchi, D.; Zangrando, E.; Mestroni, G.; Milani, B.; Gladiali, S.; Carfagna, C.; Binotti, B.; Bronco, S.; Gragnoli, T. J. Organomet. Chem. 2005, 690, 2106-2120.
47. Durand, J.; Zangrando, E.; Stener, M.; Fronzoni, G.; Carfagna, C.; Binotti, B.; Kamer, P. C. J.; Mueller, C.; Caporali, M.; vanLeeuwen, P. W. N. M.; Vogt, D.; Milani, B. Chem. Eur. J. 2006, 12, 7639-7651.
48. Gsponer, A.; Milani, B.; Consiglio, G. Helv. Chim. Acta 2002,85, 4074-4078.
49. Binotti, B.; Carfagna, G; Zuccaccia, C.; Macchioni, A. Chem. Commun. 2005, 92-94.
50. Binotti, B.; Bellachioma, G.; Cardaci, G.; Carfagna, C.; Zuccaccia, C; Macchioni, A. Chem. Eur. J. 2007, 13, 1570-1582.
51. Scarel, A.; Durand, J.; Franchi, D.; Zangrando, E.; Mestroni, G.; Carfagna, C.; Mosca, L.; Seraglia, R.; Consiglio, G.; Milani, B. Chem. Eur. J. 2005, 11, 6014-6023.
52. Macchioni, A.; Bellachioma, G.; Cardaci, G.; Travaglia, M.; Zuccaccia, C.; Milani, B.; Corso, G.; Zangrando, E.; Mestroni, G.; Carfagna, C.; Formica, M. Organometallies 1999, 18, 3061-3069.
53. Mul, W. P.; van der Made, A. W.; Smaardijk, A. A.; Drent, E. Catalytic Synthesis of Copolymers and Terpolymers; Kluwer Academic Publishers: Dordrecht, 2003; pp 87-140.
54. Macchioni, A.; Romani, A.; Zuccaccia, C.; Guglielmetti, G.; Querci, C. Organometallies 2003, 22, 1526-1533.
55. Haga, N.; Takayanagi, H.; Tokumaru, K. J. Chem. Soc, Perkin Trans. 2202, 2, 734-745.
56. Nagel, M.; Sen, A. Organometallics 2006, 25, 4722-4724.
57. Sen, A.; Borkar, S. J. Organomet. Chem. 2007, 692, 3291-3299.
58. Milani, B.; Corso, G.; Mestroni, G.; Carfagna, C.; Formica, M.; Seraglia, R. Organometallics 2000, 19, 3435-3441.
59. Mecca, T.; Superchi, S.; Giorgio, E.; Rosini, C. Tetrahedron: Aysmmetry 2001, 12, 1225-1233.
60. Otwinowski, Z.; Minor, W. Macromolecular Crystallography, part A; Academic Press: New York, 1997; Vol. 276, pp 307-326.
61. Sheldrick, G. M. SHELX97 Programs for Crystal Structure Analysis (Release 97-2); University of Göttingen, 1998.
62. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.