Mechanism of methylacetylene bisselenation catalyzed by palladium complex from density functional study

Journal of Computational Chemistry

Volumn 32, Issue 6, 2011, Pages 1170-1177

  Wang, Meiyan ^a,c   Cheng, Lin ^a   Wang, Jinping ^b   Wu, Zhijian ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b QINGDAO AGRICULTURAL UNIVERSITY   (China)

^c HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

density functional method; methylacetylene bisselenation; Pd complex; reaction mechanism

Indexed keywords

DENSITY-FUNCTIONAL METHODS; DENSITY-FUNCTIONAL STUDY; ELECTRONIC MECHANISMS; FRONTIER MOLECULAR ORBITALS; INSERTION PROCESS; METHYLACETYLENE; METHYLACETYLENE BISSELENATION; OVERALL REACTIONS; OXIDATIVE ADDITIONS; PALLADIUM COMPLEXES; PD COMPLEX; REACTION MECHANISM; REDUCTIVE ELIMINATION; SUBSTITUTED CARBONS;

CARBON MONOXIDE; CATALYSIS; COMPLEXATION; MOLECULAR ORBITALS;

PALLADIUM COMPOUNDS;

ALKYNE; CARBON MONOXIDE; ORGANOMETALLIC COMPOUND; PALLADIUM; PROPYNE; SELENIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; QUANTUM THEORY;

ALKYNES; CARBON MONOXIDE; CATALYSIS; ORGANOMETALLIC COMPOUNDS; PALLADIUM; QUANTUM THEORY; SELENIUM COMPOUNDS;

EID: 79952527364     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.21700     Document Type: Article

References (62)

1. Beletskaya, I. P.; Ananikov, V. P., Eur J Org Chem 2007, 3431.
2. Freudendahl, D. M.; Shahzad, S. A.; Wirth, T., Eur J Org Chem 2009, 1649.
3. Ogawa, A., J Organomet Chem 2000, 611, 463.
4. Alonso, F.; Beletskaya, I. P.; Yus, M., Chem Rev 2004, 104, 3079.
5. Kondo, T.; Mitsudo, T., Chem Rev 2000, 100, 3205.
6. Han, L.-B.; Tanaka, M., Chem Commun 1999, 395.
7. Beletskaya, I.; Moberg, C., Chem Rev 1999, 99, 3435.
8. Beletskaya, I.; Moberg, C., Chem Rev 2006, 106, 2320.
9. Perin, G.; Lenardão, E. J.; Jacob, R. G.; Panatieri, R. B., Chem Rev 2009, 109, 1277.
10. Kuniyasu, H.; Kambe, N.,; Chem Lett 2006, 35, 1320.
11. Hegedus, L. L.; McCabe, R. W., Catalyst Poisoning; Marcel Dekker: New York, 1984.
12. Kuniyasu, H.; Ogawa, A.; Miyazaki, S.-I.; Ryu, I.; Kambe, N.; Sonoda, N., J Am Chem Soc 1991, 113, 9796.
13. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T., J Am Chem Soc 1997, 119, 123801.
14. Xiao, W.-J.; Alper, H., J Org Chem 2005, 70, 1802.
15. Kawakami, J.; Mihara, M.; Kamiya, I.; Takeba, M.; Ogawa, A.; Sonoda, N., Tetrahedron 2003, 59, 3521.
16. Kawakami, J.; Takeba, M.; Kamiya, I.; Sonoda, N.; Ogawa, A., Tetrahedron 2003, 59, 6559.
17. Ogawa, A.; Takeba, M.; Kawakami, J.; Ryu, I.; Kambe, N.; Sonoda, N., J Am Chem Soc 1995, 117, 7564.
18. Kajitani, M.; Kamiya, I.; Nomoto, A.; Kihara, N.; Ogawa, A., Tetrahedron 2006, 62, 6355.
19. Ogawa, A.; Kawakami, J.; Sonoda, N.; Hirao, T., J Org Chem 1996, 61, 4161.
20. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N., J Am Chem Soc 1992, 114, 5902.
21. Ananikov, V. P.; Orlov, N. V.; Beletskaya, I. P.; Khrustalev, V. N.; Antipin, M. Y.; Timofeeva, T. V., J Am Chem Soc 2007, 129, 7252.
22. Ananikov, V. P.; Orlov, N. V.; Beletskaya, I. P., Organometallics 2006, 25, 1970.
23. Ananikov, V. P.; Malyshev, D. A.; Beletskaya, I. P.; Aleksandrov, G. G.; Eremenko, I. L., Adv Synth Catal 2005, 347, 1993.
24. Ogawa, A.; Ikeda, T.; Kimura, K.; Hirao, T., J Am Chem Soc 1999, 121, 5108.
25. Arisawa, M.; Yamaguchi, M., Org Lett 2001, 3, 763.
26. Zou, K. B.; Yin, X. H.; Liu, W. Q.; Qiu, R. H.; Li, R. X.; Shao, L. L.; Li, Y. H.; Xu, X. H.; Yang, R. H., Synth Commun 2009, 39, 2464.
27. Arisawa, M.; Suwa, A.; Fujimoto, K.; Yamaguchi, M., Adv Synth Catal 2003, 345, 560.
28. Kodama, S.; Nishinaka, E.; Nomoto, A.; Sonoda, M.; Ogawa, A., Tetrahedron Lett 2007, 48, 6312.
29. Ananikov, V. P.; Orlov, N. V.; Kabeshov, M. A.; Beletskaya I. P.; Starikova, Z. A., Organometallics 2008, 27, 4056.
30. Ananikov, V. P.; Kabeshov, M. A.; Beletskaya, I. P.; Aleksandrov, G. G.; Eremenko, I. L., J Organomet Chem 2003, 687, 451.
31. Ananikov, V. P., Kabeshov, M. A.; Beletskaya, I. P.; Khrustalev, V. N.; Antipin, M. Y., Organometallics 2005, 24, 1275.
32. Ananikov, V. P.; Beletskaya, I. P., Org Biomol Chem 2004, 2, 284.
33. Ananikov, V. P.; Gayduk, K. A.; Beletskaya, I. P.; Khrustalev, V. N.; Antipin, M. Y., Chem Eur J 2008, 14, 2420.
34. Gonzales, J. M.; Musaev, D. G.; Morokuma, K., Organometallics 2005, 24, 4908.
35. Cai, M.; Wang Y.; Hao, W., Green Chem 2007, 9, 1180.
36. Kamiya, I.; Nishinaka, E.; Ogawa, A., J Org Chem 2005, 70, 696.
37. Ananikov, V. P.; Malyshev, D. A.; Beletskaya, I. P.; Aleksandrov, G. G.; Eremenko, I. L., J Organomet Chem 2003, 679, 162.
38. Ogawa, A.; Kudo, A.; Hirao, T., Tetrahedron Lett 1998, 39, 5213.
39. Ananikov, V. P.; Orlov, N. V.; Beletskaya, I. P., Organometallics 2007, 26, 740.
40. Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Sonoda, N., Tetrahedron Lett 1992, 33, 5525.
41. Nakata, N.; Uchiumi, R.; Yoshino, T.; Ikeda, T.; Kamon, H.; Ishii, A., Organometallics 2009, 28, 1981.
42. Ananikov, V. P.; Beletskaya, I. P.; Aleksandrov, G. G.; Eremenko, I. L., Organometallics 2003, 22, 1414.
43. Kamiya, I.; Nishinaka, E.; Ogawa, A., Tetrahedron Lett 2005, 46, 3649.
44. Ogawa, A.; Yokoyama, K.; Yokoyama, H.; Sekiguchi, M.; Kambe, N.; Sonoda, N., Tetrahedron Lett 1990, 31, 5931.
45. Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N., Organometallics 1992, 11, 3937.
46. Ananikov, V. P.; Orlov, N. V.; Beletskaya, I. P., Russ Chem Bull Int Ed 2005, 54, 576.
47. Toyofuku, M.; Murase, E.; Fujiwara, S.; Shin-ike, T.; Kuniyasu, H.; Kambe, N., Org Lett 2008, 10, 3957.
48. Wang, M. Y.; Cheng, L.; Hong, B.; Wu, Z. J., Organometallics 2009, 28, 1506.
49. Wang, M. Y.; Cheng, L.; Wu, Z. J., Dalton Trans 2008, 3879.
50. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, J.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A., Gaussian 03, Gaussian, Inc.: Pittsburgh, PA, 2003.
51. Becke, A. D., Phys Rev A 1988, 38, 3098.
52. Lee, C.; Yang, W.; Parr, R. G., Phys Rev B 1988, 37, 785.
53. Becke, A. D., J Chem Phys 1993, 98, 5648.
54. Hay, P. J.; Wadt, W. R., J Chem Phys 1985, 82, 299.
55. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G., Chem Phys Lett 1993, 208, 111.
56. Huzinaga, S., Ed. Gaussian Basis Sets for Molecular Calculations; Elsevier Science Pub. Co.: Amsterdam, 1984.
57. Fukui, K., Acc Chem Res 1981, 14, 363.
58. Barone, V.; Cossi, M. J., Phys Chem A 1998, 102, 1995.
59. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V., J Comput Chem 2003, 24, 669.
60. Wang, M. Y.; Cheng, L.; Hong, B.; Wu, Z. J., J Comput Chem 2009, 30, 1521.
61. Kuniyasu, H.; Maruyama, A.; Kurosawa, H., Organometallics 1998, 17, 908.
62. Kuniyasu, H.; Hiraike, H.; Morita, M.; Tanaka, A.; Sugoh, K.; Kurosawa, H., J Org Chem 1999, 64, 7305.