Gold(i)-catalyzed cycloaddition of 1-(1-Alkynyl)cyclopropyl ketones with nucleophiles to yield substituted furans: A DFT study

Organometallics

Volumn 28, Issue 11, 2009, Pages 3129-3139

  Zhang, Jinsheng ^a,b   Shen, Wei ^a   Li, Longqin ^a   Li, Ming ^a  

^a SOUTHWEST UNIVERSITY   (China)

^b GUIZHOU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ALKYNYL; BENT BONDS; CYCLOPROPYL KETONES; DFT STUDY; ION PAIRS; ORBITAL ENERGY; PROTON MIGRATION; PROTON SHUTTLE; REACTION BARRIERS; SOLVENT EFFECTS; STEREOSPECIFIC; STEREOSPECIFIC ADDITION; THEORETICAL STUDY; TRIFLUOROMETHANE; TRIPLE BONDS;

ADDITION REACTIONS; CATALYSIS; CATALYST REGENERATION; COORDINATION REACTIONS; DENSITY FUNCTIONAL THEORY; GOLD COMPOUNDS; KETONES; METHANOL; PROBABILITY DENSITY FUNCTION; PROPANE; PROTONS;

NUCLEOPHILES;

EID: 66349094524     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om801115a     Document Type: Article

References (51)

1. Mondal, S.; Nogami, T.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2003, 68, 9496-9498.
2. Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955-2020.
3. Keay, B. A. Chem. Soc. Rev. 1999, 28, 209-215.
4. Lipshutz, B. H. Chem. Rev. 1986, 86, 795-819.
5. Xiao, Y.; Zhang, J. Angew. Chem., Int. Ed. 2008, 47, 1903-1906.
6. Zhang, J.; Schmalz, H. G. Angew. Chem., Int. Ed. 2006, 45, 6704- 6707.
7. Patil, N. T.; Wu, H.; Yamamoto, Y. J. Org. Chem. 2005, 70, 4531-4534.
8. Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95-98.
9. Cacchi, S. J. Organomet. Chem. 1999, 576, 42-64.
10. Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288.
11. Marshall, J. A.; Bartley, G. S. J. Org. Chem. 1994, 59, 7169-7171.
12. Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816-5819.
13. Hou, X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon Press: Oxford, U.K., 2002; Vol. 14, pp 139-179.
14. Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 960-969.
15. Dudnik, A. S.; Gevorgyan, V. Angew. Chem. 2007, 119, 5287- 5289.
16. Aponick, A.; Li, C.; Biannic, B. Org. Lett. 2008, 10(4), 669-671.
17. Grisé, C. M.; Rodrigue, E. M.; Barriault, L. Tetrahedron 2008, 64, 797-808.
18. Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804-16805.
19. Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500-10501.
20. Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel'in, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440-1452.
21. Xia, Y.; Dudnik, A. S.; Gevorgyan, V.; Li, Y. J. Am. Chem. Soc. 2008, 130, 6940-6941.
22. Lemière, G.; Gandon, V.; Agenet, N.; Goddard, J. P.; de Kozak, A.; Aubert, C.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2006, 45, 7596-7599.
23. Shi, F.; Li, X.; Xia, Y.; Zhang, L.; Yu, Z. J. Am. Chem. Soc. 2007, 129, 15503-15512.
24. Cheong, P. H.; Morganelli, P.; Luzung, M. R.; Houk, K. N.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 4517-4526.
25. -catalyzed reaction pathways are more favored than the cation [AuL]+-catalyzed channels. The effect of the different ligands on the reaction is remarkable. The proton migration by two nucleophilic molecules MeOH appears easier.
26. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496-499.
27. 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.; Bakken, V.; 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, S.; 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, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
28. Parr, R. G.; Yang, W. Density-functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
29. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
30. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
31. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
32. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-297.
33. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
34. 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, 111-114.
35. Faza, O. N.; Lopez, C. S.; Álvarez, R.; de Lera, A. R. J. Am. Chem. Soc. 2006, 128, 2434-2437.
36. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem. Int. Ed. 2004, 43, 2402- 2406.
37. Roithová, J.; Hrus?ák, J.; Schröder, D.; Schwarz, H. Inorg. Chim. Acta 2005, 358, 4287-4292.
38. Joshi, A. M.; Delgass, W. N.; Thomson, K. T. J. Phys. Chem. B 2006, 110, 2572-2581.
39. Nieto-Oberhuber, C.; López, S.; Jiménez-Núñez, E.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 5916-5923.
40. Kovács, G.; Ujaque, G.; Lledós, A. J. Am. Chem. Soc. 2008, 130, 853-864.
41. Zhang, J.; Shen, W.; Li, M. Eur. J. Org. Chem. 2007, 29, 4855-4866.
42. Gonzalez, C.; Schlegel, H. B. J. Phsy. Chem. 1990, 94, 5523-5527.
43. Flükiger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. MOLEKEL 4.3; Swiss Center for Scientific Computing: Manno, Switzerland, 2000/2002.
44. Portmann, S.; Lüthi, H. P. Chimia 2000, 54, 766-770.
45. Carpenter, J. E.; Weinhold, F. J. Mol. Struct. (THEOCHEM) 1988, 169, 41-50.
46. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. ReV. 1988, 88, 899-926.
47. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211- 7218.
48. Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245.
49. Gorelsky, S. I.; Lever, A. B. P. J. Organomet. Chem. 2001, 635, 187-196.
50. Gorelsky, S. I. AOMix: Program for Molecular Orbital Analysis; York University: Toronto, Canada, 1997; http://www.sf-chem.net/.
51. Gorelsky, S. I.; Ghosh, S.; Solomon, E. I. J. Am. Chem. Soc. 2006, 128, 278-290.