Aryl-substituted cyclopropyl acetylenes as sensitive mechanistic probes in the gold-catalyzed hydration of alkynes. comparison to the Ag(I)-, Hg(II)-, and Fe(III)-catalyzed processes

Journal of Organic Chemistry

Volumn 78, Issue 17, 2013, Pages 8880-8884

  Velegraki, Georgia ^a   Stratakis, Manolis ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCATIONS; CYCLOPROPYL; ELECTRONIC DIFFERENCES; MECHANISTIC PROBES; METHYL KETONES; SENSITIVE PROBE;

ACETYLENE; GOLD; HYDRATION; KETONES; LIGHTING; MERCURY (METAL); PROBES;

CATALYSIS;

2 PHENYLCYCLOPROPYL ACETYLENE; 2,2 DIPHENYLCYCLOPROPYL ACETYLENE; ACETYLENE DERIVATIVE; ALKYNE; FERRIC ION; GOLD; MERCURY; METAL; SILVER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDRATION; PROTON NUCLEAR MAGNETIC RESONANCE;

ALKYNES; CATALYSIS; FERRIC COMPOUNDS; GOLD; MERCURY; MOLECULAR STRUCTURE; SILVER; VINYL COMPOUNDS; WATER;

EID: 84883813820     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401325t     Document Type: Article

References (49)

1. Bandini, M. Chem. Soc. Rev. 2011, 40, 1358
2. Corma, A.; Leyva-Perez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657
3. Lu, B.-L.; Dai, L.; Shi, M. Chem. Soc. Rev. 2012, 41, 3318
4. Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448
5. Stratakis, M.; Garcia, H. Chem. Rev. 2012, 112, 4469
6. Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395
7. Hintermann, L.; Labonne, A. Synthesis 2007, 1121
8. Brenzovich, W. E., Jr. Angew. Chem., Int. Ed. 2012, 51, 8933
9. Leyva, A.; Corma, A. J. Org. Chem. 2009, 74, 2067
10. Marion, N.; Ramon, R. S.; Nolan, S. P. J. Am. Chem. Soc. 2009, 131, 448
11. Hashmi, A. S. K.; Hengst, T.; Lothschutz, C.; Rominger, F. Adv. Synth. Catal. 2010, 352, 1315
12. Wetzel, C.; Kunz, P. C.; Thiel, I.; Spingler, R. Inorg. Chem. 2011, 50, 7863
13. Ghosh, N.; Nayak, S.; Sahoo, A. K. J. Org. Chem. 2011, 76, 500
14. Dunsford, J. J.; Cavell, K. J.; Kariuki, B. M. Organometallics 2012, 31, 4118
15. Gomez-Suarez, A.; Oonishi, Y.; Meiries, S.; Nolan, S. P. Organometallics 2013, 32, 1106
16. Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729
17. Casado, R.; Contel, M.; Laguna, M.; Romero, P.; Sanz, S. J. Am. Chem. Soc. 2003, 125, 11925
18. Wang, W.; Jasinski, J.; Hammond, G. B.; Xu, B. Angew. Chem., Int. Ed. 2010, 49, 7247
19. Lein, M.; Rudolph, M.; Hashmi, A. S. K.; Schwerdtfeger, P. Organometallics 2010, 29, 2206
20. Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415
21. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563
22. Roembke, P.; Schmidbaur, H.; Cronje, S.; Raubenheimer, H. J. Mol. Catal. A: Chem. 2004, 212, 35
23. Sanz, S.; Jones, L. A.; Mohr, F.; Laguna, M. Organometallics 2007, 26, 952
24. Carriedo, G. A.; Lopez, S.; Suarez-Suarez, S.; Presa-Soto, D.; Presa-Soto, A. Eur. J. Inorg. Chem. 2011, 1442
25. Wang, D.; Cai, R.; Sharma, S.; Jirak, J.; Thummanapelli, S. K.; Akhmedov, N. G.; Zhang, H.; Liu, X.; Petersen, J. L.; Shi, X. J. Am. Chem. Soc. 2012, 134, 9012
26. Roithova, J.; Jankova, S.; Jasikova, L.; Vana, J.; Hybelbauerova, S. Angew. Chem., Int. Ed. 2012, 51, 8378
27. Krauter, C. M.; Hashmi, A. S. K.; Pernpointner, M. ChemCatChem 2010, 2, 1226
28. Mazzone, G.; Russo, N.; Sicilia, E. Organometallics 2012, 31, 3074
29. Garcia-Mota, M.; Cabello, N.; Maseras, F.; Echavarren, A. M.; Perez-Ramirez, J.; Lopez, N. ChemPhysChem 2008, 9, 1624
30. Milnes, K. K.; Jennings, M. C.; Baines, K. M. J. Am. Chem. Soc. 2006, 128, 2491
31. Schmittel, M.; Mahajan, A. A.; Bucher, G.; Bats, J. W. J. Org. Chem. 2007, 72, 2166
32. Hurni, K. L.; Baines, K. M. Chem. Commun. 2011, 47, 8382
33. Kotzabasaki, V.; Lykakis, I. N.; Gryparis, C.; Psyllaki, A.; Vasilikogiannaki, E.; Stratakis, M. Organometallics 2013, 32, 665
34. Gottschling, S. E.; Grant, T. N.; Milnes, K. K.; Jennings, M. C.; Baines, K. M. J. Org. Chem. 2005, 70, 2686
35. Thuong, M. B. T.; Mann, A.; Wagner, A. Chem. Commun. 2012, 48, 434
36. Cabrero-Antonino, J. R.; Leyva-Perez, A.; Corma, A. Chem.-Eur. J. 2012, 18, 11107
37. Nishizawa, M.; Skwarczynski, M.; Imagawa, H.; Sugihara, T. Chem. Lett. 2002, 31, 12
38. Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162
39. Kulinkovich, O. G.; Tischenko, I. G.; Sviridov, S. V. Zh. Org. Khim. 1987, 23, 982
40. Nakamura, H.; Tashiro, S.; Kamakura, T. Tetrahedron Lett. 2005, 46, 8333
41. Alberti, M. N.; Orfanopoulos, M. Org. Lett. 2008, 10, 2465
42. Glass, A. C.; Morris, B. B.; Zakharov, L. N.; Liu, S.-Y. Org. Lett. 2008, 10, 4855
43. Yamamoto, Y. Chem. Rev. 2008, 108, 3199
44. Leyva-Perez, A.; Corma, A. Angew. Chem., Int. Ed. 2012, 51, 614
45. Mantecon, S.; Vaquero, J. J.; Alvarez-Builla, J.; de la Puente, M. L.; Espinosa, J. F.; Ezquerra, J. Org. Lett. 2003, 5, 3791
46. Pennell, M. N.; Turner, P. G.; Sheppard, T. D. Chem.-Eur. J. 2012, 18, 4748
47. Das, A.; Dash, C.; Yousufuddin, M.; Celik, M. A.; Frenking, G.; Dias, H. V. R. Angew. Chem., Int. Ed. 2012, 51, 3940
48. Brown, T. J.; Widenhoefer, R. A. J. Organomet. Chem. 2011, 696, 1216
49. Solladie-Cavallo, A.; Isarno, T. Tetrahedron Lett. 1999, 40, 1579