Computational study of copper-free sonogashira cross-coupling reaction

Organometallics

Volumn 30, Issue 21, 2011, Pages 5656-5664

  Sikk, Lauri ^a   Tammiku Taul, Jaana ^a   Burk, Peeter ^a  

^a UNIVERSITY OF TARTU   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

CIS-TRANS ISOMERIZATION; COMPUTATIONAL STUDIES; COPPER-FREE SONOGASHIRA; DICHLOROMETHANE SOLUTIONS; OXIDATIVE ADDITIONS; PHENYLACETYLENES; REACTION MECHANISM; REACTION MIXTURE; REDUCTIVE ELIMINATION; SEC-BUTYLAMINE; TETRAKIS;

ACETYLENE; AROMATIC HYDROCARBONS; BROMINE COMPOUNDS; DICHLOROMETHANE; ISOMERIZATION; ORGANOMETALLICS;

ADDITION REACTIONS;

EID: 80755169909     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om2004817     Document Type: Article

References (49)

1. Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259-263.
2. Cassar, L. J. Organomet. Chem. 1975, 93, 253-257.
3. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470.
4. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1470.
5. Kotschy, A.; Timári, G. Heterocycles Trans. Met. Catal. 2005, 199.
6. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017.
7. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49.
8. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340-1341.
9. Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834-871.
10. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874-922.
11. Komáromi, A.; Tolnai, G. L.; Novák, Z. Tetrahedron Lett. 2008, 49, 7294-7298.
12. Amatore, C.; Carré, E.; Jutand, A. Acta Chem. Scand. 1998, 52, 100-106.
13. Fitton, P.; Rick, E. A. J. Organomet. Chem. 1971, 28, 287-291.
14. Grushin, V. V. Organometallics 2000, 19, 1888-1900.
15. Jutand, A.; Négri, S.; Principaud, A. Eur. J. Inorg. Chem. 2005, 631-635.
16. Nozima, H.; Kawata, N.; Nakamura, Y.; Maruya, K.; Mizoroki, T.; Ozaki, A. Chem. Lett. 1973, 1163-1164.
17. Amatore, C.; Bensalem, S.; Ghalem, S.; Jutand, A. J. Organomet. Chem. 2004, 689, 4642-4646.
18. Heiden, M. an der; Plenio, H. Chem. Commun. 2007, 972-974.
19. Ljungdahl, T.; Bennur, T.; Dallas, A.; Emtenäs, H.;Mårtensson, J. Organometallics 2008, 27, 2490-2498.
20. Tougerti, A.; Negri, S.; Jutand, A. Chem.-Eur. J. 2007, 13, 666-676.
21. Chen, L.-P.; Hong, S.-G.; Hou, H.-Q. Chin. J. Struct. Chem. 2008, 27, 1404-1411.
22. Fairlamb, I. J. S.; O'Brien, C. T.; Lin, Z.; Lam, K. C. Org. Biomol. Chem. 2006, 4, 1213-1216.
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.;Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc., Wallingford, CT, 2009.
24. Becke, A. D. J. Chem. Phys. 1997, 107, 8554-8560.
25. Grimme, S. J. Comput. Chem. 2006, 2007, 1787-1799.
26. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007-1023.
27. Schuchardt, K. L.; Didier, B. T.; Elsethagen, T.; Sun, L.; Gurumoorthi, V.; Chase, J.; Li, J.; Windus, T. L. J. Chem. Inf. Model 2007, 47, 1045-1052.
28. Feller, D. J. Comput. Chem. 1996, 17, 1571-1586.
29. Ardura, D.; López, R.; Sordo, T. L. J. Phys. Chem. B 2005, 109, 23618-23623.
30. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
31. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1991, 95, 5853-5860.
32. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396.
33. Cramer, C. J. Essentials of Computational Chemistry: Theories and Models; Wiley: New York, USA, 2003.
34. Shaik, S.; Kozuch, S. J. Am. Chem. Soc. 2006, 128, 3355-3365.
35. Kozuch, S.; Shaik, S. J. Phys. Chem. A 2008, 112, 6032-6041.
36. Uhe, A.; Kozuch, S.; Shaik, S. J. Comput. Chem. 2011, 32, 978-985.
37. Amatore, C.; Pfluger, F. Organometallics 1990, 9, 2276-2282.
38. Sergienko, V. S.; Porai-Koshits, M. A. J. Struct. Chem. 1988, 28, 548-552.
39. Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319-2330.
40. Gooßen, L. J.; Koley, D.; Hermann, H.; Thiel, W. Chem. Commun. 2004, 2141-2143.
41. Amatore, C.; Jutand, A; Lemaitre, F.; Lucricard, J.; Kozuch, S.; Shaik, S. J. Organomet. Chem. 2004, 689, 3728-3734.
42. Barrios-Landeros, F.; Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 5842-5843.
43. Casado, A. L.; Espinet, P. Organometallics. 1998, 17, 954-959.
44. Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2005, 24, 2398-2410.
45. Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647-3658.
46. Jovera, J.; Feya, N.; Purdieb, M.; Lloyd-Jonesa, G. C.; Harveya, J. N. J. Mol. Catal. A: Chem. 2010, 324, 39-47.
47. Huang, Y.;Weng,C.;Hong, F. Chem.-Eur. J. 2008, 14, 4426-4434.
48. Grushin, V. V.; Alper, H. Organometallics 1996, 15, 5242-5245.
49. Pérez-Rodríguez, M.; Braga, A. A. C.; Garcia-Melchor, M.; Pérez-Temprano,M.H.;Casares, J. A.;Ujaque, G.; Lera, A. R. de; Álvarez, R.; Maseras, F.; Espinet, P. J. Am. Chem. Soc. 2009, 131, 3650-3657.