Exploring electronic and steric effects on the insertion and polymerization reactivity of phosphinesulfonato pdii catalysts

Chemistry - A European Journal

Volumn 19, Issue 52, 2013, Pages 17773-17788

  Neuwald, Boris ^a   Falivene, Laura ^b   Caporaso, Lucia ^b   Cavallo, Luigi ^c   Mecking, Stefan ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b UNIVERSITY OF SALERNO   (Italy)

^c KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

Author keywords

catalysis; coordination modes; density functional calculations; kinetics; reaction mechanisms; theoretical chemistry

Indexed keywords

COORDINATION MODES; DENSITY-FUNCTIONAL CALCULATIONS; POLYMER MICROSTRUCTURES; POLYMER MOLECULAR WEIGHT; POLYMERIZATION BEHAVIOR; POLYMERIZATION REACTIVITY; REACTION MECHANISM; THEORETICAL CHEMISTRY;

CATALYSIS; CATALYST DEACTIVATION; CHLORINE COMPOUNDS; COORDINATION REACTIONS; COPOLYMERIZATION; COPOLYMERS; DENSITY FUNCTIONAL THEORY; ENZYME KINETICS; ETHYLENE; MOLECULAR WEIGHT; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS; POLYMERS; RATE CONSTANTS; REACTION KINETICS; SULFUR DIOXIDE;

CATALYST ACTIVITY;

EID: 84890985064     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301365     Document Type: Article

References (68)

1. L. K. Johnson, S. Mecking, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 267-268.
2. S. Mecking, L. K. Johnson, L. Wang, M. Brookhart, J. Am. Chem. Soc. 1998, 120, 888-899.
3. E. Drent, R. v. Dijk, R. v. Ginkel, B. v. Oort, R. I. Pugh, Chem. Commun. 2002, 744-745.
4. T. Kochi, S. Noda, K. Yoshimura, K. Nozaki, J. Am. Chem. Soc. 2007, 129, 8948-8949.
5. K. Nozaki, S. Kusumoto, S. Noda, T. Kochi, L. W. Chung, K. Morokuma, J. Am. Chem. Soc. 2010, 132, 16030-16042.
6. S. Ito, K. Munakata, A. Nakamura, K. Nozaki, J. Am. Chem. Soc. 2009, 131, 14606-14607.
7. T. Rünzi, D. Fröhlich, S. Mecking, J. Am. Chem. Soc. 2010, 132, 17690-17691.
8. A. Berkefeld, S. Mecking, Angew. Chem. 2008, 120, 2572-2576
9. Angew. Chem. Int. Ed. 2008, 47, 2538-2542
10. A. Nakamura, S. Ito, K. Nozaki, Chem. Rev. 2009, 109, 5215-5244
11. E. Y. X. Chen, Chem. Rev. 2009, 109, 5157-5214
12. D. Takeuchi, Dalton Trans. 2010, 39, 311-328.
13. T. Rünzi, U. Tritschler, P. Roesle, I. Göttker-Schnetmann, H. M. Möller, L. Caporaso, A. Poater, L. Cavallo, S. Mecking, Organometallics 2012, 31, 8388-8406.
14. D. Guironnet, P. Roesle, T. Rünzi, I. Göttker-Schnetmann, S. Mecking, J. Am. Chem. Soc. 2009, 131, 422-423.
15. B. Neuwald, F. Ölscher, I. Göttker-Schnetmann, S. Mecking, Organometallics 2012, 31, 3128-3137.
16. D. Guironnet, L. Caporaso, B. Neuwald, I. Göttker-Schnetmann, L. Cavallo, S. Mecking, J. Am. Chem. Soc. 2010, 132, 4418-4426.
17. P. Braunstein, C. Frison, X. Morise, Angew. Chem. 2000, 112, 2989-2992
18. Angew. Chem. Int. Ed. 2000, 39, 2867-2870
19. M. Agostinho, P. Braunstein, Chem. Commun. 2007, 58-60.
20. L. Piche, J.-C. Daigle, G. Rehse, J. P. Claverie, Chem. Eur. J. 2012, 18, 3277-3285.
21. L. Piche, J.-C. Daigle, R. Poli, J. P. Claverie, Eur. J. Inorg. Chem. 2010, 4595-4601.
22. N. T. Allen, B. L. Goodall, L. H. McIntosh, EP1760086A2, 2007.
23. T. M. J. Anselment, C. Wichmann, C. E. Anderson, E. Herdtweck, B. Rieger, Organometallics 2011, 30, 6602-6611.
24. K. M. Skupov, P. R. Marella, M. Simard, G. P. A. Yap, N. Allen, D. Conner, B. L. Goodall, J. P. Claverie, Macromol. Rapid Commun. 2007, 28, 2033-2038.
25. L. K. Johnson, C. M. Killian, M. Brookhart, J. Am. Chem. Soc. 1995, 117, 6414-6415.
26. T. K. Woo, T. Ziegler, J. Organomet. Chem. 1999, 591, 204-213.
27. Z. Shen, R. F. Jordan, J. Am. Chem. Soc. 2010, 132, 52-53.
28. D. Guironnet, T. Rünzi, I. Göttker-Schnetmann, S. Mecking, Chem. Commun. 2008, 4965-4967.
29. E. Drent, R. v. Dijk, R. v. Ginkel, B. v. Oort, R. I. Pugh, Chem. Commun. 2002, 964-965.
30. J. Vela, G. R. Lief, Z. Shen, R. F. Jordan, Organometallics 2007, 26, 6624-6635.
31. A. K. Hearley, R. J. Nowack, B. Rieger, Organometallics 2005, 24, 2755-2763.
32. W. N. Chou, M. Pomerantz, J. Org. Chem. 1991, 56, 2762-2769.
33. T. Rünzi, D. Guironnet, I. Göttker-Schnetmann, S. Mecking, J. Am. Chem. Soc. 2010, 132, 16623-16630.
34. B. Neuwald, L. Caporaso, L. Cavallo, S. Mecking, J. Am. Chem. Soc. 2013, 135, 1026-1036.
35. A. Berkefeld, S. Mecking, J. Am. Chem. Soc. 2009, 131, 1565-1574.
36. A. C. Albéniz, P. Espinet, R. Lopez-Fernandez, Organometallics 2003, 22, 4206-4212.
37. M. Nagel, A. Sen, Organometallics 2006, 25, 4722-4724.
38. P. Wucher, L. Caporaso, P. Roesle, F. Ragone, L. Cavallo, S. Mecking, I. Göttker-Schnetmann, Proc. Natl. Acad. Sci. USA 2011, 108, 8955-8959.
39. Z. Cai, Z. Shen, X. Zhou, R. F. Jordan, ACS Catal. 2012, 2, 1187-1195.
40. S. D. Ittel, L. K. Johnson, M. Brookhart, Chem. Rev. 2000, 100, 1169-1204.
41. T. Friedberger, P. Wucher, S. Mecking, J. Am. Chem. Soc. 2012, 134, 1010-1018.
42. A. Poater, B. Cosenza, A. Correa, S. Giudice, F. Ragone, V. Scarano, L. Cavallo, Eur. J. Inorg. Chem. 2009, 1759-1766.
43. L. Cavallo, A. Correa, C. Costabile, H. Jacobsen, J. Organomet. Chem. 2005, 690, 5407-5413.
44. A. Poater, F. Ragone, S. Giudice, C. Costabile, R. Dorta, S. P. Nolan, L. Cavallo, Organometallics 2008, 27, 2679-2681.
45. A. Poater, L. Cavallo, Dalton Trans. 2009, 41, 8885-8890.
46. F. Ragone, A. Poater, L. Cavallo, J. Am. Chem. Soc. 2010, 132, 4249-4258.
47. A. Poater, F. Ragone, R. Mariz, R. Dorta, L. Cavallo, Chem. Eur. J. 2010, 16, 14348-14353.
48. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
49. A. Haras, G. D. W. Anderson, A. Michalak, B. Rieger, T. Ziegler, Organometallics 2006, 25, 4491-4497.
50. 3], which increases the stability of this intermediate, see
51. C. Pellecchia, A. Immirzi, A. Zambelli, J. Organomet. Chem. 1994, 479, C 9 -C 11.
52. A. G. Wong-Foy, G. Bhalla, X. Y. Liu, R. A. Periana, J. Am. Chem. Soc. 2003, 125, 14292-14293
53. J. Oxgaard, R. P. Muller, W. A. Goddard, R. A. Periana, J. Am. Chem. Soc. 2004, 126, 352-363
54. G. Bhalla, X. Y. Liu, J. Oxgaard, W. A. Goddard, R. A. Periana, J. Am. Chem. Soc. 2005, 127, 11372-11389.
55. D. P. Gates, S. A. Svejda, E. Oñate, C. M. Killian, L. K. Johnson, P. S. White, M. Brookhart, Macromolecules 2000, 33, 2320-2334.
56. C. Popeney, Z. Guan, Organometallics 2005, 24, 1145-1155.
57. C. S. Popeney, Z. Guan, Macromolecules 2010, 43, 4091-4097.
58. W. L. Armarego, D. D. Perrin, Purification of Laboratory Chemicals, 4 thed., Elsevier, Burlington, 1996.
59. E. V. Salo, Z. Guan, Organometallics 2003, 22, 5033-5046.
60. Stoe X-RED Ver. 1.3, Data Reduction Programm Darmstadt, Germany, 2005.
61. G.M. Sheldrick, SHELXS-97, Program for Crystal Structure Analysis, Universität Göttingen, Göttingen, 1986.
62. G.M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, Universität Göttingen, Göttingen, 1997.
63. K. Brandenburg, Diamond Ver. 3.0a, Crystal Impact GbR, Bonn, 2005.
64. Gaussian 09, Revision D.01, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, Jr., J.A. Montgomery, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.
65. A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100
66. J. P. Perdew, Phys. Rev. B 1986, 34, 7406
67. J. P. Perdew, Phys. Rev. B 1986, 33, 8822-8824.
68. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.