Stille cross-coupling reactions of alkenylstannanes with alkenyl iodides mediated by copper(I) thiophene-2-carboxylate: A density functional study

Organometallics

Volumn 29, Issue 14, 2010, Pages 3077-3084

  Wang, Meiyan ^a   Lin, Zhenyang ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

A-DENSITY; ALKENYL; ALKENYLSTANNANES; CARBOXYLATE LIGANDS; COUPLING PRODUCT; DENSITY FUNCTIONAL THEORY CALCULATIONS; DFT CALCULATION; N-METHYLPYRROLIDONE; ONE-STEP PROCESS; OXIDATIVE ADDITIONS; REACTION MECHANISM; REDUCTIVE ELIMINATION; SOLVENT MOLECULES; STILLE CROSS-COUPLING; TRANSMETALATION; VINYL IODIDES;

CARBOXYLATION; CHEMICAL BONDS; THIOPHENE;

DENSITY FUNCTIONAL THEORY;

EID: 77955908205     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100304t     Document Type: Article

References (64)

1. (a) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
2. (b) Duncton, M. A. J.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1999, 1, 1235.
3. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
4. (b) Fugami, K.; Kosugi, M. Top. Curr. Chem. 2002, 219, 87.
5. (c) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 4.
6. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359.
7. Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 118.
8. (a) Konig, CM.; Gebhardt, B.; Schleth, C.; Dauber, M.; Koert, U. Org. Lett. 2009, 11, 2728.
9. (b) Falck, J. R.; Patel, P. K.; Bandyopadhyay, A. J. Am. Chem. Soc. 2007, 129, 790.
10. (c) Wehlan, H.; Dauber, M.; Fernaud, M.-T. M.; Schuppan, J.; Mahrwald, R.; Ziemer, B.; Garcia, M.-E. J.; Koert, U. Angew. Chem., Int. Ed. 2004, 43, 4597.
11. (d) Paterson, I.; Lombart, H.-G.; Allerton, C. Org. Lett. 1999, 1, 19.
12. (e) Borsato, G.; Lucchi, O. D.; Fabris, F.; Groppo, L.; Lucchini, V; Zambon, A. J. Org. Chem. 2002, 67, 7894.
13. (f) Paterson, I.; Britton, R.; Delgado, O.; Meyer, A.; Poullennec, K. G. Angew. Chem., Int. Ed. 2004, 43, 43.
14. (g) Maleczka, R. E., Jr.; Terrell, L. R.; Geng, F.; Ward, J. S., III. Org. Lett. 2002, 4, 2841.
15. (h) Paterson, I.; Man, J. Ttrahedron Lett. 1997, 38, 695.
16. (i) Paterson, I.; Gardner, N. M.; Poullennec, K. G.; Wright, A. E. Boorg. Med. Chem. Lett. 2007, 17, 17.
17. (j) Paterson, I.; Gardner, N. M.; Poullennec, K. G.; Wright, A. E. J. Nat. Prod. 2008, 71, 364.
18. (k) Paterson, I.; Doughty, V. A.; McLeod, M. D.; Trieselmann, T. Angew. Chem., Int. Ed. 2000, 39, 1308.
19. (l) Furstner, A.; Funel, J.-A; Tremblay, M.; Bouchez, L. C.; Nevado, C.; Waser, M.; Ackerstaff, J.; Stimson, C. C. Chem. Commun. 2008, 2873.
20. (a) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333.
21. (b) Hodgkinson, R. C.; Schulz, J.; Willis, M. C. Org. Biomol. Chem. 2009, 7, 432.
22. (c) Furstner, A.; Dierkes, T.; Thiel, O. R.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286.
23. (d) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem., Int. Ed. 2002, 41, 3701.
24. (e) Shen, R.; Lin, C. T.; Bowman, E. J.; Bowman, B. J.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 7889.
25. (f) Su, Q.; Panek, J. S. J. Am. Chem. Soc. 2004, 126, 2425.
26. (g) Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 6040.
27. (h) Shen, R.; Lin, C. T.; Porco, J. A., Jr. J Am Cem. Soc. 2002, 124, 124.
28. (i) Trost, B. M.; Stiles, D. T. Org. Lett. 2005, 7, 2117.
29. (j) Wang, X.; Bowman, E. J.; Bowman, B. J.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 3601.
30. (a) Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
31. (b) Babudri, F.; Cardone, A.; Farinola, G. M.; Naso, F. Ttrahedron 1998, 54, 14609.
32. (a) Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4, 983.
33. (b) Yang, H.; Liebeskind, L. S. Org. Lett. 2007, 9, 2993.
34. (c) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.
35. (d) Mee, S. P. H.; Lee, V; Baldwin, J. E.. J. E. A. Chem. Soc. 2007, 129, 1132.
36. (e) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979.
37. Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91.
38. Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3, 2149.
39. Thasana, N.; Worayuthakarn, R.; Kradanrat, P.; Hohn, E.; Young, L.; Ruchirawat, S. J. Org. Chem. 2007, 72, 9379.
40. Xue, L.; Lin, Z. Chem. Soc. Rev. 2010, 39, 1692.
41. Zhang, S.-L.; Liu, L.; Fu, Y.; Guo, Q.-X. Organometallics 2007, 26, 4546.
42. Mayoral, J. A.; Rodríguez-Rodríguez, S.; Salvatella, L. Chem.-Eur. J. 2008, 14, 9274.
43. (a) Fraile, J. M.; García, J. I.; Gil, M. J.; Martínez- Merino, V.; Mayoral, J. A.; Salvatella, L. Chem.-Eur. J. 2004, 10, 758.
44. (b) García, J. I.; Jiménez-Osés, G.; Martínez-Merino, V.; Mayoral, J. A.; Pires, E.; Villalba, I. Chem-Eur. J. 2007, 13, 4064.
45. Ahlquist, M.; Nielsen, T. E.; Quement, S. L.; Tanner, D.; Norrby, P.-O. Chem.-Eur. J. 2006, 12, 2866.
46. Musaev, D. G.; Liebeskind, L. S. Organometallics 2009, 28, 28.
47. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
48. (b) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Cem. Phys. Lett. 1989, 157, 157.
49. (c) Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785.
50. (d) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. J. Phys. Chem. 1994, 98, 11623.
51. (a) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 82.
52. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
53. (a) Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033.
54. (b) Hay, P. J. J. Chem. Phys. 1977, 66, 4377.
55. Huzinaga, S. Gaussian Basis Sets for Molecular Calculations; Elsevier Science Pub. Co.: Amsterdam, 1984.
56. (a) Fukui, K. J. Phys. Chem. 1970, 74, 4161.
57. (b) Fukui, K. Acc. Chem. Res. 1981, 14, 363.
58. Frisch, M. J.; et al. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
59. Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647.
60. Wang, Y.; Burton, D. J. Org. Lett. 2006, 8, 1109.
61. (a) Kang, S.-K.; Kim, J.-S.; Choi, S.-C. J. Org. Chem. 1997, 62, 4208.
62. (b) Kang, S.-K; Kim, J.-S.; Yoon, S.-K.; Lim, K.-H.; Yoon, S. S. Ttrahedron Lett. 1998, 39, 3011.
63. Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033.
64. Ananikov, V. P.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 2002, 124, 2839.