DFT studies on copper-catalyzed hydrocarboxylation of alkynes using CO 2 and hydrosilanes

Organometallics

Volumn 32, Issue 18, 2013, Pages 5224-5230

  Fan, Ting ^a   Sheong, Fu Kit ^a   Lin, Zhenyang ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

COMPETITIVE REACTIONS; DFT CALCULATION; DFT STUDY; HYDROCARBOXYLATION; HYDROSILANES; REACTION MECHANISM;

CATALYSIS; COPPER; DENSITY FUNCTIONAL THEORY; HYDROCARBONS; HYDROSILYLATION;

CARBON DIOXIDE;

EID: 84884636766     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om4008532     Document Type: Article

References (56)

1. Markewitz, P.; Kuckshinrichs, W.; Leitner, W.; Linssen, J.; Zapp, P.; Bongartz, R.; Schreiber, A.; Mε̈ller, T. E. Energy Environ. Sci. 2012, 5, 7281
2. Wang, W.; Wang, S.; Ma, X.; Gong, J. Chem. Soc. Rev. 2011, 40, 3703
3. Yu, K. M. K.; Curcic, I.; Gabriel, J.; Tsang, S. C. E. ChemSusChem 2008, 1, 893
4. Mikkelsen, M.; Jørgensen, M.; Krebs, F. C. Energy Environ. Sci. 2010, 3, 43
5. Omae, I. Coord. Chem. Rev. 2012, 256, 1384
6. Wiliams, C. M.; Johnson, J. B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936
7. Correa, A.; Martin, R. J. Am. Chem. Soc. 2009, 131, 15974
8. Mori, M. Eur. J. Org. Chem. 2007, 4981
9. Takimoto, M.; Kajima, Y.; Sato, Y.; Mori, M. J. Org. Chem. 2005, 70, 8605
10. Ochiai, H.; Jang, M.; Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2008, 10, 2681
11. Fillon, H.; Gosmini, C.; Périchon, J. J. Am. Chem. Soc. 2003, 125, 3867
12. Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2008, 130, 15254
13. Takaya, J.; Iwasawa, N. Org. Lett. 2011, 13, 1698
14. Fujihara, T.; Xu, T.; Semba, K.; Terao, J.; Tsuji, Y. Angew. Chem., Int. Ed. 2011, 50, 523
15. Zhang, Y.; Riduan, S. N. Angew. Chem., Int. Ed. 2011, 50, 6210
16. Motokura, K.; Kashiwame, D.; Miyaji, A.; Baba, T. Org. Lett. 2012, 14, 2642
17. Marciniec, B. Coord. Chem. Rev. 2005, 249, 2374
18. Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161
19. Marciniec, B. Hydrosilylation of Alkenes and Their Derivatives Adv. Silicon Sci. 2009, 1, 3-51
20. Fujihara, T.; Tani, Y.; Semba, K.; Terao, J.; Tsuji, Y. Angew. Chem., Int. Ed. 2012, 51, 11487
21. Fleming, I.; Roessler, F. J. Chem. Soc., Chem. Commun. 1980, 276
22. Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc., Perkin Trans. 2 1981, 2527
23. Deutsch, C.; Krause, N.; Lipshutz, B. H. Chem. Rev. 2008, 108, 2916
24. Herron, J. R.; Ball, Z. T. J. Am. Chem. Soc. 2008, 130, 16486
25. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
26. Wachters, A. J. H. Chem. Phys. 1970, 52, 1033
27. Hay, P. J. J. Chem. Phys. 1977, 66, 4377
28. Fukui, K. J. Phys. Chem. 1970, 74, 4161
29. Fukui, K. Acc. Chem. Res. 1981, 14, 363
30. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995
31. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669
32. Benson, S. W. The Foundations of Chemical Kinetics; Krieger: Malabar, FL, 1982.
33. Okuno, Y. Chem. Eur. J. 1997, 3, 212
34. Ardura, D.; López, R.; Sordo, T. L. J. Phys. Chem. B. 2005, 109, 23618
35. Schoenebeck, F.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 2496
36. Liu, Q.; Lan, Y.; Liu, J.; Li, G.; Wu, Y.-D.; Lei, A. J. Am. Chem. Soc. 2009, 131, 10201
37. Ariafard, A.; Brookes, N. J.; Stanger, R.; Yates, B. F. Organometallics 2011, 30, 1340
38. Yu, H.; Lu, Q.; Dang, Z.; Fu, Y. Chem. Asian J. 2013, 8, 8
39. Ariafard, A.; Ghohe, N. M.; Abbasi, K. K.; Canty, A. J.; Yates, B. F. Inorg. Chem. 2013, 52, 707-717
40. Frisch, M. J. Gaussian 03, revision B05; Gaussian, Inc., Pittsburgh, PA, 2003.
41. Zhao, H. T.; Lin, Z.; Marder, T. B. J. Am. Chem. Soc. 2006, 128, 15637
42. Dang, L.; Zhao, H. T.; Lin, Z.; Marder, T. B. Organometallics 2008, 27, 1178
43. Zhao, H. T.; Dang, L.; Marder, T. B.; Lin, Z. J. Am. Chem. Soc. 2008, 130, 5586
44. Kleeberg, C.; Dang, L.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. Engl. 2009, 48, 5350
45. Iseenhuth, J.-T.; Dagorne, S.; Bellemin-Laponnaz S. C. R. Chimie 2010, 13, 353
46. Fujihara, T.; Semba, K.; Terao, J.; Tsuji, Y. Angew. Chem. 2010, 122, 1514
47. Welle, A.; Díez-González, S.; Tinant, B.; Nolan, S. P.; Riant, O. Org. Lett. 2006, 8, 6059
48. Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182
49. Issenhuth, J. T.; Dagorne, S.; Bellemin-Laponnaz, S. Adv. Synth. Catal. 2006, 348, 1991
50. Rendler, S.; Plefka, O.; Karatas, B.; Auer, G.; Fröhlich, R.; Mück-Lichtenfeld, C.; Grimme, S.; Oestreich, M. Chem. Eur. J. 2008, 14, 11512
51. Kaur, H.; Zinn, F. K.; Stevens, E. D.; Nolan, S. P. Organometallics 2004, 23, 1157
52. Díez-González, S.; Scott, N. M.; Nolan, S. P. Organometallics 2006, 25, 2355
53. Díez-González, S.; Escudero-Adán, E. C.; Benet-Buchholz, J.; Stevens, E. D.; Slawin, A. M. Z.; Nolan, S. P. Dalton Trans. 2010, 39, 7595
54. Díez-González, S.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 349
55. Deutsch, C.; Lipshutz, B. H.; Krause, N. Angew. Chem., Int. Ed. 2007, 46, 1650
56. Dean, J. A. Lange's handbook of chemistry; McGraw Hill: New York, 1985; pp 4.41-4.53.